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Showing papers in "Tetrahedron Letters in 1990"


Journal ArticleDOI
TL;DR: NIS together with a catalytic amount of trifluoromethanesulfonic acid proved to be very convenient for the rapid, high-yielding and stereoselective (1,2-trans) glycosidation of esterified thioglycosides with glycosyl acceptors.

744 citations


Journal ArticleDOI
TL;DR: PyBOP as discussed by the authors, an analog of BOP where dimethylamino groups are replaced with pyrrolidino, is the only analog exhibiting equivalent properties in peptide bond formation.

596 citations


Journal ArticleDOI
Ryo Irie1, K. Noda1, Yoshio Ito1, Naohide Matsumoto1, Tsutomu Katsuki1 
TL;DR: Manganese complex of the optically active salen ligand [ N,N '-bis[(S )-3-(1-phenylpropyl)salicylidene]-(1 R,2 R )-1,2-diphenylethylenediaminato] was found to be an effective catalyst for the enantioselective epoxidation of olefins as discussed by the authors.

586 citations


Journal ArticleDOI
TL;DR: In this paper, N-Iodosuccinimide/trifluoromethanesulfonic acid, which had been shown to promote the solvolysis of disarmed n-pentenyl glycosides, was found to induce the same reactivity with disarmed thioglycosides as substrates.

508 citations


Journal ArticleDOI
TL;DR: Bisoxazolines (1, 7) prepared from diethyl malonate and chiral amino alcohols were converted into their Cu(II) complexes which, upon activation, exhibit high enantioselectivity of up to 99 %ee for catalytic cyclopropanation of olefins as discussed by the authors.

468 citations


Journal ArticleDOI
TL;DR: In this article, the stereochemistry of many alternating (1,3,5...) polyol chains can be determined by preparation and 13C NMR analysis of two frame-shifted polyacetonide derivatives.

446 citations


Journal ArticleDOI
TL;DR: Rychnovsky's recent correlation of the stereochemistry-dependent 13 C NMR chemical shifts of 4,6-disubstituted 1,3-diol acetonides with diol stereochemistry may be extended to more highly substituted dioxolanes bearing substituents in the 5-position as discussed by the authors.

291 citations


Journal ArticleDOI
TL;DR: Tertiary amine oxides have been utilized to effect cobalt-mediated intramolecular cyclizations of enynes (Pauson-Khand reactions) at room temperature as discussed by the authors.

281 citations


Journal ArticleDOI
TL;DR: In this article, a specific glycosidation of partially-benzoylated thioglycosides with perbenzylated donors was demonstrated in the presence of the promotor iodonium dicollidine perchlorate.

274 citations


Journal ArticleDOI
TL;DR: In this article, the reduction of a variety of achiral ketones with catecholborane as stoichiometric reductant and 0.1 equiv of oxazaborolidine 2 as catalyst in toluene at −78°C proceeds in > 95% yield and with enantioselectivities in the range 30:1 to 9: 1, depending on substrate.

234 citations


Journal ArticleDOI
TL;DR: In this paper, the oxazaphopholidine borano complex was described and the preparation of (+) and (−)-PAMP 7a, DIPAMP 9a or β-BNPE 9b from the same complex was discussed.

Journal ArticleDOI
TL;DR: In this article, neutral and basic amino acid residues at the N-terminus of α-hydroxy-β-amino dimethyl phosphonate were incorporated in a tripeptidic framework suitable for the aspartyl protease renin.

Journal ArticleDOI
TL;DR: Preliminary studies indicate that the new analog induces the differentiation of human leukemia HL-60 cells, with little or no calcemic activity.

Journal ArticleDOI
TL;DR: In this paper, the major phytoalexin of oat leaves is not the 4-H-3,1-benzoxazin-4 one previously reported, but the corresponding amide.

Journal ArticleDOI
TL;DR: Sodium triacetoxyborohydride is a reagent of choice in the reductive amination of aldehydes and saturated aliphatic ketones with primary and secondary amines as mentioned in this paper.

Journal ArticleDOI
TL;DR: Isoazolidines are reductively cleaved to 1,3-amino alcohols by reacting with Mo(CO)6 and water as mentioned in this paper. Reaction conditions are simple, mild and selective giving good yields of highly functionalized products with complete retention of configuration of the stereocenters.

Journal ArticleDOI
TL;DR: In this article, Nα-Fmoc protected amino acid derivatives with hydroxyl-functions provided by polystyrene and cellulose derived support materials are achieved in high yields with 2,4,6-masitylenesulfonyl-3-nitro-1,2,4-triazelide (MSNT) in the presence of 1-methyltmidazole (MeIm).

Journal ArticleDOI
TL;DR: In this article, a method for aminolysis of 1,2-epoxides by means of metal salts is described, which is a simple, efficient, inexpensive, anti stereoselective, and highly regi-lective method.

Journal ArticleDOI
TL;DR: In this article, a convenient method has been developed for direct conversion of nitriles to amidines in high yields, which can also be applied to the preparation of guanidines from N-alkyl cyanamides.

Journal ArticleDOI
TL;DR: In this article, the 3,6-bis[trifluoromethyl] -et-[methoxycarbonyl]-1,2,4,5-tetrazines were reactivated with dienophiles.

Journal ArticleDOI
TL;DR: A new convenient strategy for functionalization of the 2-position of cyclodextrins involving deprotonation ofcyclodextrin by sodium hydride followed by a nucleophilic attack of the resultant cyclodeXTrin oxyanion on the desired electrophile gives a high yield of the cyclodeixxtrin derivative.

Journal ArticleDOI
TL;DR: In this paper, a power-variable electrophilic trifluoromethylating agent was developed for the first time, which was shown to be a good electrophlic reagent.

Journal ArticleDOI
TL;DR: Thiols and selenols are smoothly oxidised in high yield to disulphides and diselenides by sodium perborate at room temperature using Na6(CO3SO4)(SO4)SO4 as oxidant.

Journal ArticleDOI
TL;DR: In this paper, X-ray diffraction analyses of sulfinamide 8 and sultam (R)-2 are presented, and the results show that sultams are highly diastereoselective.

Journal ArticleDOI
TL;DR: Preparation of the spiro beta-lactam 7 and its evaluation as a poliovirus and human rhinovirus 3C-proteinase inhibitor is described.

Journal ArticleDOI
TL;DR: In this paper, the design and synthesis of new fluorogenic substrate probes for HIV protease based on resonance energy transfer arc was described, and these substrates permit sensitive, continuous measurement of protease activity.

Journal ArticleDOI
TL;DR: In this article, the presence of biphenylenediol 8 accelerates the rate of some Diels-Alder reactions, and a complex involving two hydrogen bonds is proposed.

Journal ArticleDOI
TL;DR: Macrolactonization of 3,5- O -(3,4-dimethoxybenzylidene)-9,11-O -(2,4,6-trimethylbenzo-idene)(9 S )-9-dihydroerythronolide A seco-acid (4 ) was reexamined under various conditions and found to proceed rapidly only by treatment of 4 with Yamaguchi's reagent, 2.4, 6-trichlorobenzoyl chloride, in the presence

Journal ArticleDOI
TL;DR: In this article, two new cytotoxic phenols, hericenone A (1 ) and B (4 ) were isolated from the mushroom Hericium erinaceum.

Journal ArticleDOI
TL;DR: In this article, the highest enantioselectivities were achieved in catalytic asymmetric dihydroxylations using potassium hexacyanoferrate(III) [potassium ferricyanide, K3Fe(CN)6] as the reoxidant.