Journal ArticleDOI
Michael reaction of functionalized chiral cyclanone imines. Enantioselective synthesis of C2-symmetric cis-(1R,6R)-1,6-dimethylbicyclo[4.4.0]decane-3,8-dione
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TLDR
In this paper, a chiral imine of 2-methylcyclohexanone having a protected carbonyl function in the 4-position 2 led to monoprotected keto ester 4 or dione 6.Abstract:
Enantioselective Michael reaction of methyl acrylate or methyl vinyl ketone with a chiral imine of 2-methylcyclohexanone having a protected carbonyl function in the 4-position 2 led to monoprotected keto ester 4 or dione 6. The latter was converted into the title compound 10.read more
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Asymmetric addition of α-branched cyclic ketones to allenamides catalyzed by a chiral phosphoric acid
Xiaoyu Yang,F. Dean Toste +1 more
TL;DR: Asymmetric addition of unactivated α-branched cyclic ketones to allenamides catalyzed by a chiral phosphoric acid catalyst, generates an all-carbon quaternary stereocenter with broad substrate scope and high enantioselectivity.
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Design and enantioselective synthesis of Cashmeran odorants by using "enol catalysis".
TL;DR: Novel Cashmeran odorants were designed by molecular modeling and realized by utilizing a new type of enol activation catalysis and affords different cyclic ketones bearing α-quaternary stereocenters in good to excellent yields and with high enantioselectivity.
Journal ArticleDOI
Rational Design of a Chiral Palladium(0) Olefin Complex of Unprecedented Stability
TL;DR: A chiral bidentate olefin ligand with a 1.4a,5,8a-tetrahydro-naphthalene-2,6-dione framework was designed in this paper.
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Enantioselective Synthesis of Quaternary Carbon Stereogenic Centers through the Primary Amine‐Catalyzed Michael Addition Reaction of α‐Substituted Cyclic Ketones at High Pressure
Ryo Horinouchi,Kouhei Kamei,Riki Watanabe,Nobushige Hieda,Naoki Tatsumi,Keiji Nakano,Yoshiyasu Ichikawa,Hiyoshizo Kotsuki +7 more
TL;DR: In this article, the enantioselective Michael addition reaction of α-substituted cyclic ketones with acrylates was efficiently promoted by a primary amine chiral catalyst under high pressure conditions (1.0 GPa) in tetrahydrofuran.
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Enantioselective synthesis of (2S4aS,8aR)-1,1,4a-trimethyldecahydronaphthalen-2-ol [(−)-TMD], (4aS,8aR)-5,5,8a-trimethyloctahydronaphthalen-2(1H)-one, and (−)-polywood®, through michael-type reaction of chiral imines
TL;DR: The title compounds 6, 15, and 17 have been synthesized in a straightforward way in good yields and high enantiomeric excesses by the chiral imines method, leading to building-blocks 2 and 10, followed by a few conventional steps as mentioned in this paper.
References
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Nucleic acid related compounds. 42. A general procedure for the efficient deoxygenation of secondary alcohols. Regiospecific and stereoselective conversion of ribonucleosides to 2'-deoxynucleosides
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Enantioselective synthesis of quaternary carbon centers through Michael-type alkylation of chiral imines
TL;DR: In this article, the cyclanones chirales disubstituees in 2,2 par alkylation were prepared for cyclanone monosubstitutes.
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Toward a transition-state model in the asymmetric alkylation of chiral ketone secondary enamines by electron-deficient alkenes. A theoretical MO study
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A Theoretical Investigation of Enantioselectivity: Michael Reaction of Secondary Enamines with Enones
TL;DR: In this article, a theoretical study of the enantioselective Michael-type addition of chiral secondary enamines to enones has been achieved, where up to 8 local energy minimums are characterized whose examination shows that no prediction can be.