Asymmetric synthesis of α-amino aldehydes from sulfinimine (N-sulfinyl imine)-derived α-amino 1,3-dithianes.: Formal synthesis of (-)-2,3-trans-3,4-cis-dihydroxyproline

被引：34

作者：

Davis, FA ^{[1
]}

Rarnachandar, T ^{[1
]}

Chai, J ^{[1
]}

Skucas, E ^{[1
]}

机构：

[1] Temple Univ, Dept Chem, Philadelphia, PA 19122 USA

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 16期

关键词：

alpha-amino aldehydes; alpha-amino alcohols; allylic amines; alpha-amino 1,3-dithianes; sulfinimines; asymmetric synthesis;

D O I：

10.1016/j.tetlet.2006.02.092

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Hydrolysis Of sulfinimine-derived N-sultinyl alpha-amino 1,3-dithianes with aqueous 1,3-dibromo-5,5-dimethylhydantoin affords the corresponding N-tosyl alpha-amino aldehydes in good yield and high enantiomeric purity. These aldehydes call be reduced to amino alcohols and undergo the Wittig reaction to give allylic amines without epimerization. The utility of this methodology is illustrated in a formal synthesis of (-)-2,3-trans-3,4-cis-dihydroxyproline. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：2743 / 2746

页数：4

共 39 条

[1]

ALEXAKIS A, 1995, SYNTHESIS-STUTTGART, P1038

[2]

BRAUN M, 1993, ANGEW CHEM INT EDIT, V32, P578, DOI 10.1002/anie.199305781

[3]

BRINGMANN G, 1989, SYNTHESIS-STUTTGART, P608

[4]

Davies SG, 2002, SYNLETT, P1146