Catalytic, enantioselective alkylations of N,O- and N,N-acetals and hemiacetals

被引：41

作者：

Ferraris, D ^{[1
]}

Young, B ^{[1
]}

Dudding, T ^{[1
]}

Drury, WJ ^{[1
]}

Lectka, T ^{[1
]}

机构：

[1] Johns Hopkins Univ, Dept Chem, Baltimore, MD 21218 USA

来源：

TETRAHEDRON | 1999年 / 55卷 / 29期

关键词：

asymmetric synthesis; amino acids; acetals; copper;

D O I：

10.1016/S0040-4020(99)00450-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report the first examples of catalytic, enantioselective alkylation of N,O-acetals to produce useful amino acid derivatives 5 in high yield (73-93%) and enantioselectivity (70-96%). We have extended the utility of our reaction to include a simple one-pot procedure from readily available starting materials. We also provide several different N-based protecting groups that greatly increase the flexibility of the reaction. In addition, we have elucidated novel mechanistic information including the discovery of unique transilylations that start off the catalytic reactions of enol silane nucleophiles with N,O-acetals. These details will guide us in further explorations of the reaction's scope and utility. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：8869 / 8882

页数：14

共 42 条

[1] CHIRAL ACETALS IN ASYMMETRIC-SYNTHESIS
ALEXAKIS, A
MANGENEY, P
[J]. TETRAHEDRON-ASYMMETRY, 1990, 1 (08) : 477 - 511
[2] BOTTING NP, 1995, CHEM SOC REV, P401
[3] Bowman WR, 1997, TETRAHEDRON, V53, P15787
[4] STEREOSELECTIVE ROUTES TO CHIRAL 2-HYDROXY-4-OXO ACIDS AND SUBSTITUTED 2-HYDROXYBUTYROLACTONES USING LACTATE-DEHYDROGENASES
CASY, G
[J]. TETRAHEDRON LETTERS, 1992, 33 (52) : 8159 - 8162
[5] COLYIN EW, 1988, SILICON REAGENTS ORG
[6] THE PREPARATION OF PURE ALLYL-TYPE AND BENZYL-TYPE ORGANOALKALI INTERMEDIATES VIA ORGANOTIN COMPOUNDS
DESPONDS, O
SCHLOSSER, M
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1991, 409 (1-2) : 93 - 101
[7] A novel synthesis of α-amino acid derivatives through catalytic, enantioselective ene reactions of α-imino esters
Drury, WJ
Ferraris, D
Cox, C
Young, B
Lectka, T
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (42) : 11006 - 11007
[8] Evans DA, 1998, ANGEW CHEM INT EDIT, V37, P3372, DOI 10.1002/(SICI)1521-3773(19981231)37:24<3372::AID-ANIE3372>3.0.CO
[9] 2-K
[10] C-2-symmetric tin(II) complexes as chiral Lewis acids. Catalytic enantioselective anti aldol additions of enolsilanes to glyoxylate and pyruvate esters
Evans, DA
MacMillan, DWC
Campos, KR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (44) : 10859 - 10860

← 1 2 3 4 5 →