Showing papers by "Teruaki Mukaiyama published in 1983"
TL;DR: In this article, α-Benzyloxy aldehydes having a chiral tertiary center at α-carbon atom are synthesized in high enantiomeric excess by successive treatment of 2-methoxycarbonyl-3-phenyl-1,3-diazabicyclo[3.3.0]octane with diisobutylaluminum hydride (DIBAL-H) and Grignard reagents.
Abstract: α-Benzyloxy aldehydes having a chiral tertiary center at α-carbon atom are synthesized in high enantiomeric excess by successive treatment of 2-methoxycarbonyl-3-phenyl-1,3-diazabicyclo[3.3.0]octane with diisobutylaluminum hydride (DIBAL-H) and Grignard reagents. The asymmetric reaction is applied to the total synthesis of exo-(+)-brevicomin.
30 citations
TL;DR: In this article, an efficient method for the acceleration of the intramolecular Diels-Alder reaction was established utilizing the internal interaction, the internal hydrogen bonding and the internal coordination of a magnesium salt.
Abstract: An efficient method for the acceleration of the intramolecular Diels-Alder reaction was established utilizing the internal interaction—the internal hydrogen bonding and the internal coordination of a magnesium salt. The intramolecular Diels-Alder reaction between nitrofuran derivatives and various acrylic acid derivatives give good yields of the cycloadducts when internal hydrogen bonding is present. When cyclic α,β-unsaturated amides are employed as dienophile, the corresponding cycloadducts are obtained in high yield utilizing internal coordination of a magnesium salt.
28 citations
TL;DR: In the presence of chiral diamine, (2S)-1-methyl-2-[(N-1-naphthylamino)methyl]pyrrolidine reacts with various α-ketoesters to afford the corres as discussed by the authors.
Abstract: In the presence of chiral diamine, (2S)-1-methyl-2-[(N-1-naphthylamino)methyl]pyrrolidine, the tin(II) enolate of 3-acetylthiazolidine-2-thione reacts with various α-ketoesters to afford the corres...
28 citations
TL;DR: Optically active bicyclic lactones are synthesized from ircides, derived from (R)-(−)-2-amino-2-phenylethanol and meso-cyclic-1,2-cis-dicarboxylic acids, by successive treatment with sodium bis(2-m...
Abstract: Optically active bicyclic lactones are synthesized from ircides, derived from (R)-(−)-2-amino-2-phenylethanol and meso-cyclic-1,2-cis-dicarboxylic acids, by successive treatment with sodium bis(2-m...
26 citations
TL;DR: In this paper, a highly enantioselective aldol-type reaction forming various β-hydroxy carbonyl compounds from 3-acetylthiazolidine-2-thione and achiral aldehydes is achieved via divalent tin enolate employing chiral diamine derived from (S)-proline as a ligand.
Abstract: A highly enantioselective aldol-type reaction forming various β-hydroxy carbonyl compounds from 3-acetylthiazolidine-2-thione and achiral aldehydes is achieved via divalent tin enolate employing chiral diamine derived from (S)-proline as a ligand.
22 citations
TL;DR: In this article, α, β-unsaturated ketones are also prepared via the Sn(II) enolate by a one-pot procedure from the corresponding saturated ketones.
Abstract: α,β-Unsaturated aldehydes are prepared by the direct dehydrogenation of the corresponding saturated aldehydes by the coupled use of PdCl2(PhCN)2–AgOSO2CF3 in the presence of N-methylmorpholine in good yields. α,β-Unsaturated ketones are also prepared via the Sn(II) enolate by a one-pot procedure from the corresponding saturated ketones.
20 citations
TL;DR: Tin(II) enolate, formed in situ by the oxidative addition of metallic tin to 2-bromo-2-methylpropanal, reacts with aldehydes to give β-hydroxy aldehyde in fairly good yields as mentioned in this paper.
Abstract: Tin(II) enolate, formed in situ by the oxidative addition of metallic tin to 2-bromo-2-methylpropanal, reacts with aldehydes to give β-hydroxy aldehydes in fairly good yields.
18 citations
TL;DR: Acylation of alcohols and amides was effected under mild conditions by the use of 1,1′-dimethylstannocene and acyl chlorides, giving the corresponding esters and imides in good to excellent yields.
Abstract: Acylation of alcohols and amides was effected under mild conditions by the use of 1,1′-dimethylstannocene and acyl chlorides, giving the corresponding esters and imides in good to excellent yields.
15 citations
TL;DR: Methylglyoxal is successfully converted to the tin(II) enediolate on treatment with activated metallic tin and reacts with several aldehydes to give α, β-dihydroxyketones in good yields.
Abstract: Methylglyoxal is successfully converted to the tin(II) enediolate on treatment with activated metallic tin. The tin(II) enediolate reacts with several aldehydes to give α, β-dihydroxyketones in good yields.
12 citations
TL;DR: In this paper, the intramolecular Diels-Alder reactions between acyclic dienes and α,β-unsaturated amides utilizing the internal coordination of the metal salts have been studied in detail.
Abstract: The intramolecular Diels-Alder reactions between acyclic dienes and α,β-unsaturated amides utilizing the internal coordination of the metal salts have been studied in detail. When the magnesium salts of N-(trans, trans-2,4-alkadienyl)-N-(2-hydroxyphenyl)acrylamide derivatives are employed, the intramolecular Diels-Alder reactions are remarkably accelerated and the corresponding cycloadducts are obtained in high yields with isomeric ratios (exo-adducts: endo-adducts) of about 3 : 2. And the same reactions of N(trans, trans-2,4-alkadienyl)-N-(2-hydroxyphenyl)-1-cyclopentenecarboxamide afford predominantly (60 : 40 to 85 : 15 selectivity) trans-fused cycloadducts (exo-adducts) in good yields.
12 citations
TL;DR: In this article, β-Xylofuranosides are synthesized in good yields by the successive treatment of the thiocarbonate, derived from 3,5-di-O-benzyl-D-xylofuranose, with methyl fluorosulfonate and hydroxy compounds in the presence of cesium fluoride.
Abstract: β-Xylofuranosides are stereoselectively synthesized in good yields by the successive treatment of the thiocarbonate, derived from 3,5-di-O-benzyl-D-xylofuranose, with methyl fluorosulfonate and hydroxy compounds in the presence of cesium fluoride.
TL;DR: In this paper, an elaboration to the branched-chain sugar, ethyl 2-C-methyl-DL-lyxofuranoside, was demonstrated, where the enolates of 1,3-dihydroxy-2-propanone derivatives react with another ketone, methyl pyruvate, under mild conditions to afford the corresponding anti-crossed aldol products in moderate to excellent yields.
Abstract: Tin(II) enolates of 1,3-dihydroxy-2-propanone derivatives react with a second ketone, methyl pyruvate, under mild conditions to afford the corresponding anti-crossed aldol products in moderate to excellent yields. Facile elaboration to the branched-chain sugar, ethyl 2-C-methyl-DL-lyxofuranoside, was demonstrated.
TL;DR: Cyanohydrin silyl ethers, prepared by trimethylsilylcyanation of glyoxylic esters, smoothly react with LDA (lithium diisopropylamide) to yield the lithium salts, which in turn react with alkyl halides such as allyl bromide to give, after acetylation, the corresponding enol acetates of α-keto esters in good yields as discussed by the authors.
Abstract: Cyanohydrin silyl ethers, prepared by trimethylsilylcyanation of glyoxylic esters, smoothly react with LDA (lithium diisopropylamide) to yield the lithium salts, which in turn react with alkyl halides such as allyl bromide to give, after acetylation, the corresponding enol acetates of α-keto esters in good yields.
TL;DR: In this article, various N-alkyl imides are easily prepared in good yields under nearly neutral conditions from equimolar amounts of cyclic acid anhydrides and primary amines by the use of 1,1′-dimethylstannocene.
Abstract: Various N-alkyl imides are easily prepared in good yields under nearly neutral conditions from equimolar amounts of cyclic acid anhydrides and primary amines by the use of 1,1′-dimethylstannocene.
TL;DR: In this article, an efficient method for the acceleration of the intramolecular Diels-Alder reaction was established utilizing the internal interaction, the internal hydrogen bonding and the internal coordination of a magnesium salt.
Abstract: An efficient method for the acceleration of the intramolecular Diels-Alder reaction was established utilizing the internal interaction—the internal hydrogen bonding and the internal coordination of a magnesium salt. The intramolecular Diels-Alder reaction between nitrofuran derivatives and various acrylic acid derivatives give good yields of the cycloadducts when internal hydrogen bonding is present. When cyclic α,β-unsaturated amides are employed as dienophile, the corresponding cycloadducts are obtained in high yield utilizing internal coordination of a magnesium salt.
TL;DR: Optically active bicyclic lactones are synthesized from ircides, derived from (R)-(−)-2-amino-2-phenylethanol and meso-cyclic-1,2-cis-dicarboxylic acids, by successive treatment with sodium bis(2-m...
Abstract: Optically active bicyclic lactones are synthesized from ircides, derived from (R)-(−)-2-amino-2-phenylethanol and meso-cyclic-1,2-cis-dicarboxylic acids, by successive treatment with sodium bis(2-m...
Journal Article•
TL;DR: In this article, the optically active 3-phenylalkanals were obtained by the reaction of alkyl halides and a chiral homoenolate equivalent derived from the cinnamyl ether 3 and potassium diisopropylamide.
Abstract: Highly optically active 3-phenylalkanals were obtained by the reaction of alkyl halides and a chiral homoenolate equivalent derived from the cinnamyl ether 3 and potassium diisopropylamide, followed by acidic hydrolysis.
TL;DR: In this paper, an elaboration to the branched-chain sugar, ethyl 2-C-methyl-DL-lyxofuranoside, was demonstrated, where the enolates of 1,3-dihydroxy-2-propanone derivatives react with another ketone, methyl pyruvate, under mild conditions to afford the corresponding anti-crossed aldol products in moderate to excellent yields.
Abstract: Tin(II) enolates of 1,3-dihydroxy-2-propanone derivatives react with a second ketone, methyl pyruvate, under mild conditions to afford the corresponding anti-crossed aldol products in moderate to excellent yields. Facile elaboration to the branched-chain sugar, ethyl 2-C-methyl-DL-lyxofuranoside, was demonstrated.
TL;DR: Dimethylstannocen (I) reagiert mit Alkoholen (II) zu ZinnUD-alkoxiden (III), die in situ mit Carbonsaurechloriden (IV) in Gegenwart von Hexamethylphosphorsauretriamid (HMPA) as mentioned in this paper umgesetzt werden.
Abstract: Dimethylstannocen (I) reagiert mit Alkoholen (II) zu ZinnUD-alkoxiden (III), die in situ mit Carbonsaurechloriden (IV) in Gegenwart von Hexamethylphosphorsauretriamid (HMPA) zu Estern (V) umgesetzt werden.
TL;DR: In this article, α-Benzyloxy aldehydes having a chiral tertiary center at α-carbon atom are synthesized in high enantiomeric excess by successive treatment of 2-methoxycarbonyl-3-phenyl-1,3-diazabicyclo[3.3.0]octane with diisobutylaluminum hydride (DIBAL-H) and Grignard reagents.
Abstract: α-Benzyloxy aldehydes having a chiral tertiary center at α-carbon atom are synthesized in high enantiomeric excess by successive treatment of 2-methoxycarbonyl-3-phenyl-1,3-diazabicyclo[3.3.0]octane with diisobutylaluminum hydride (DIBAL-H) and Grignard reagents. The asymmetric reaction is applied to the total synthesis of exo-(+)-brevicomin.
TL;DR: In this paper, a highly enantioselective aldol-type reaction forming various β-hydroxy carbonyl compounds from 3-acetylthiazolidine-2-thione and achiral aldehydes is achieved via divalent tin enolate employing chiral diamine derived from (S)-proline as a ligand.
Abstract: A highly enantioselective aldol-type reaction forming various β-hydroxy carbonyl compounds from 3-acetylthiazolidine-2-thione and achiral aldehydes is achieved via divalent tin enolate employing chiral diamine derived from (S)-proline as a ligand.
TL;DR: In this paper, 2-Benzyloxycarbonylamino-2-deoxy-D-ribose was conveniently synthesized via α-chloro-β-hydroxyester prepared from 2,3-O-isopropylidene-d-glyceraldehyde and ethoxyacetylene by the stereoselective aldol reaction.
Abstract: 2-Benzyloxycarbonylamino-2-deoxy-D-ribose was conveniently synthesized via α-chloro-β-hydroxyester prepared from 2,3-O-isopropylidene-D-glyceraldehyde and ethoxyacetylene by the stereoselective aldol reaction.
TL;DR: In this paper, a cross aldol reaction between aromatic ketones and various aldehydes is achieved via divalent tin enolates employing chiral diamines derived from (S)-proline as ligands.
Abstract: Highly enantioselective cross aldol reaction between aromatic ketones and various aldehydes is achieved via divalent tin enolates employing chiral diamines derived from (S)-proline as ligands.
TL;DR: In this article, the tin enolates, formed from stannous triflate and ketones, react with a second ketone under mild conditions to afford the corresponding cross-aldol products in good to excellent yields.
Abstract: Divalent tin enolates, formed from stannous triflate and ketones, react with a second ketone under mild conditions to afford the corresponding cross-aldol products in good to excellent yields. In the case of the cross-coupling with aromatic ketone, enhanced threo-selectivity was observed.
TL;DR: Divalent tin enolates, formed from stannous triflate and 3-acylthiazolidine-2-thiones, react with aldehydes to afford the corresponding aldol products in high yields with high erythroselectivities as mentioned in this paper.
Abstract: Divalent tin enolates, formed from stannous triflate and 3-acylthiazolidine-2-thiones, react with aldehydes to afford the corresponding aldol products in high yields with high erythroselectivities. The adducts are easily transformed into β-hydroxy aldehyde and β-hydroxy carboxylic acid derivatives.