Enantioselective synthesis of cis-(2S,3R)- and trans-(2S,3S)-piperidinedicarboxylic acids using domino: allylic acetate and Ireland-Claisen rearrangements and Michael addition as the key steps

被引：14

作者：

Garrido, Narciso M. ^{[1
]}

Rosa Sanchez, M. ^{[1
]}

Diez, David ^{[1
]}

Sanz, Francisca ^{[2
]}

Urones, Julio G. ^{[1
]}

机构：

[1] Univ Salamanca, Dept Quim Organ, E-37008 Salamanca, Spain

[2] Univ Salamanca, Serv Rayos X, Fac Ciencias Quim, E-37008 Salamanca, Spain

来源：

TETRAHEDRON-ASYMMETRY | 2011年 / 22卷 / 08期

关键词：

BAYLIS-HILLMAN REACTION; BETA-AMINO ACIDS; ASYMMETRIC-SYNTHESIS; DICARBOXYLIC-ACIDS; DERIVATIVES; ANALOGS; CIS;

D O I：

10.1016/j.tetasy.2011.04.015

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

An enantioselective synthesis of (2S,3R)-piperidine-2,3-dicarboxylic acid and (2S,3.9-piperidine-2,3-dicarboxylic acid is described. This synthesis was mainly based on a delta-amino acid formation via a domino reaction: allylic acetate rearrangement, stereoselective Ireland-Claisen rearrangement and asymmetric Michael addition protocol from a Baylis-Hillman adduct, in which the cinnamaldehyde double bond is a masked carboxylic functionality, and a cerium(IV) ammonium nitrate promoted monodebenzylation. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：872 / 880

页数：9

共 34 条

[31]

SCOTT JW, 1967, TETRAHEDRON LETT, P2381

[32] SYNTHESIS OF 3(S)-PHOSPHONOACETYL-2(R)-PIPERIDINECARBOXYLIC ACID - A CONFORMATIONALLY-RESTRICTED GLUTAMATE ANTAGONIST [J].

WHITTEN, JP ;

MUENCH, D ;

CUBE, RV ;

NYCE, PL ;

BARON, BM ;

MCDONALD, IA .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1991, 1 (09) :441-444

[33] Asymmetric synthesis of trans-2,3-piperidinedicarboxylic acid and trans-3,4-piperidinedicarboxylic acid derivatives [J].

Xue, CB ;

He, XH ;

Roderick, J ;

Corbett, RL ;

Decicco, CP .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (03) :865-870

[34] THE THERMAL, ALIPHATIC CLAISEN REARRANGEMENT [J].

ZIEGLER, FE .

CHEMICAL REVIEWS, 1988, 88 (08) :1423-1452

← 1 2 3 4 →