Proline-catalyzed, asymmetric Mannich reactions in the synthesis of a DPP-IV inhibitor

被引：89

作者：

Janey, JM ^{[1
]}

Hsiao, Y ^{[1
]}

Armstrong, JD ^{[1
]}

机构：

[1] Merck & Co Inc, Merck Res Labs, Dept Process Res, Rahway, NJ 07065 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 01期

关键词：

D O I：

10.1021/jo0519458

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A. highly stereoselective L-proline-catalyzed, asymmetric direct Mannich reaction between a glyoxalate-derived imine and phenyl acetaldehyde was employed for the formation of a syn substituted beta-phenyl homoserine. This Mannich adduct was then readily elaborated to a functionalized beta-phenyl aspartic acid derivative through a series of mild and efficient transformations.

引用

页码：390 / 392

页数：3

共 15 条

[1] Asymmetric synthesis of quaternary α- and β-amino acids and β-lactams via proline-catalyzed Mannich reactions with branched aldehyde donors [J].

Chowdari, NS ;

Suri, JT ;

Barbas, CF .

ORGANIC LETTERS, 2004, 6 (15) :2507-2510

[2]

Chowdari NS, 2003, SYNLETT, P1906

[3] Direct organocatalytic asymmetric Mannich-type reactions in aqueous media:: one-pot Mannich-allylation reactions [J].

Córdova, A ;

Barbas, CF .

TETRAHEDRON LETTERS, 2003, 44 (09) :1923-1926

[4] A highly enantioselective route to either enantiomer of both α- and β-amino acid derivatives [J].

Córdova, A ;

Watanabe, S ;

Tanaka, F ;

Notz, W ;

Barbas, CF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (09) :1866-1867

[5] A highly enantioselective amino acid-catalyzed route to functionalized α-amino acids [J].

Córdova, A ;

Notz, W ;

Zhong, GF ;

Betancort, JM ;

Barbas, CF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (09) :1842-1843

[6] Discovery of potent and selective orally bioavailable β-substituted phenylalanine derived dipeptidyl peptidase IV inhibitors [J].

Edmondson, SD ;

Mastracchio, A ;

Duffy, JL ;

Eiermann, GJ ;

He, HB ;

Ita, I ;

Leiting, B ;

Leone, JF ;

Lyons, KA ;

Makarewicz, AM ;

Patel, RA ;

Petrov, A ;

Wu, JK ;

Nancy, AT ;

Weber, AE .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (12) :3048-3052

[7] Application of high pressure induced by water-freezing to the direct catalytic asymmetric three-component List- Barbas-Mannich reaction [J].

Hayashi, Y ;

Tsuboi, W ;

Shoji, M ;

Suzuki, N .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (37) :11208-11209

[8] The proline-catalyzed direct asymmetric three-component Mannich reaction: Scope, optimization, and application to the highly enantioselective synthesis of 1,2-amino alcohols [J].

List, B ;

Pojarliev, P ;

Biller, WT ;

Martin, HJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (05) :827-833

[9] The direct catalytic asymmetric three-component Mannich reaction [J].

List, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (38) :9336-9337

[10] The direct organocatalytic asymmetric Mannich reaction: Unmodified aldehydes as nucleophiles [J].

Notz, W ;

Tanaka, F ;

Watanabe, S ;

Chowdari, NS ;

Turner, JM ;

Thayumanavan, R ;

Barbas, CF .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (25) :9624-9634

← 1 2 →