Chiral heterocyclic β-enamino esters:: convenient synthesis and diastereoselective reduction

被引：35

作者：

Calvet, S ^{[1
]}

David, O ^{[1
]}

Vanucci-Bacqué, C ^{[1
]}

Fargeau-Bellassoued, MC ^{[1
]}

Lhommet, G ^{[1
]}

机构：

[1] Univ Paris 06, CNRS, Lab Chim Heterocycles, UMR 7611, F-75252 Paris 05, France

来源：

TETRAHEDRON | 2003年 / 59卷 / 33期

关键词：

pyrrolidine; piperidine; enamino ester; beta-keto ester; reduction; debenzylation;

D O I：

10.1016/S0040-4020(03)00980-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The preparation of chiral pyrrolidine and piperidine beta-enamino esters starting from omega-halogeno beta-keto esters, their diastereoselective reduction and the subsequent cleavage of the chiral auxiliary are described. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：6333 / 6339

页数：7

共 20 条

[1] Andrés JM, 2000, EUR J ORG CHEM, V2000, P1719
[2] Total synthesis of (-)-lasubine II by the conjugate addition and intramolecular acylation of an amino ester with an acetylenic sulfone
Back, TG
Hamilton, MD
[J]. ORGANIC LETTERS, 2002, 4 (10) : 1779 - 1781
[3] Chiral cyclic beta-amino esters .1. Synthesis by diastereospecific alkylation.
Bardou, A
Celerier, JP
Lhommet, G
[J]. TETRAHEDRON LETTERS, 1997, 38 (49) : 8507 - 8510
[4] BERTHIAUME G, 1995, B SOC CHIM FR, V132, P371
[5] Chirospecific syntheses of conformationally constrained 7-azabicycloheptane amino acids by transannular alkylation
Campbell, JA
Rapoport, H
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (18) : 6313 - 6325
[6] METHYL-METHACRYLATE AS ACCEPTOR IN THE ASYMMETRIC MICHAEL REACTION USING CHIRAL BETA-ENAMINOESTERS - SIMULTANEOUS, COMPLETE STEREOCONTROL OF A QUATERNARY CARBON CENTER AND A TERTIARY ONE IN THE BETA-POSITION
CAVE, C
DALEY, V
DANGELO, J
GUINGANT, A
[J]. TETRAHEDRON-ASYMMETRY, 1995, 6 (01) : 79 - 82
[7] Stereoselective reduction of enantiopure beta-enamino esters by hydride: A convenient synthesis of both enantiopure beta-amino esters
Cimarelli, C
Palmieri, G
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (16) : 5557 - 5563
[8] A short and convenient synthesis of chiral heterocyclic β-enamino esters from halogeno acetylenic esters
David, O
Fargeau-Bellassoued, MC
Lhommet, G
[J]. TETRAHEDRON LETTERS, 2002, 43 (19) : 3471 - 3474
[9] Studies towards the preparation of sparteine-like diamines for asymmetric synthesis
Harrison, JR
O'Brien, P
Porter, DW
Smith, NM
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (24): : 3623 - 3631
[10] Asymmetric synthesis of β-amino acids by addition of chiral enolates to nitrones via N-acyloxyimininm ions
Kawakami, T
Ohtake, H
Arakawa, H
Okachi, T
Imada, Y
Murahashi, S
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2000, 73 (11) : 2423 - 2444

← 1 2 →