The Growing Synthetic Utility of the Weinreb Amide

被引：241

作者：

Balasubramaniam, Sivaraman ^{[1
]}

Aidhen, Indrapal Singh ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Madras 600036, Tamil Nadu, India

来源：

SYNTHESIS-STUTTGART | 2008年 / 23期

关键词：

Weinreb amide; Grignard addition; ketones; aldehydes; acylation;

D O I：

10.1055/s-0028-1083226

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-Methoxy-N-methylamide, popularly addressed as the Weinreb amide, has surfaced as an amide with a difference. This amide has served as an excellent acylating, agent for organolithium or organomagnesium reagents and as a robust equivalent for an aldehyde group. These two aspects have been exploited exhaustively in various synthetic endeavors. This review presents the growing synthetic utility of the Weinreb amide not only in academic circles, but also its popular use on kilogram scale by various pharmaceutical industries across the globe.

引用

页码：3707 / 3738

页数：32

共 258 条

[1] Diastereoselective synthesis of 2-monosubstituted and 2,6-disubstituted piperidines [J].

Abrunhosa-Thomas, Isabelle ;

Roy, Olivier ;

Barra, Marielle ;

Besset, Tatiana ;

Chalard, Pierre ;

Troin, Yves .

SYNLETT, 2007, (10) :1613-1615

[2] Tetrahedral intermediates in reactions of carboxylic acid derivatives with nucleophiles [J].

Adler, M ;

Adler, S ;

Boche, G .

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 2005, 18 (03) :193-209

[3]

Agami C, 2002, EUR J ORG CHEM, V2002, P29, DOI 10.1002/1099-0690(20021)2002:1<29::AID-EJOC29>3.0.CO

[4]

2-B

[5] Cyclization of a chiral oxazolidine as a key-step for the synthesis of functionalized piperidines [J].

Agami, C ;

Couty, F ;

Mathieu, H .

TETRAHEDRON LETTERS, 1996, 37 (23) :4001-4002

[6] SN2′ regio and stereoselective alkylation of allylic and propargylic mesylates linked to a N-Boc oxazolidine using organocuprates [J].

Agami, C ;

Couty, F ;

Evano, G ;

Mathieu, H .

TETRAHEDRON, 2000, 56 (03) :367-376

[7] A NOVEL SYNTHESIS OF BENZOCYCLOBUTENONES [J].

AIDHEN, IS ;

AHUJA, JR .

TETRAHEDRON LETTERS, 1992, 33 (37) :5431-5432

[8]

AIDHEN IS, UNPUB

[9] Versatility of Weinreb amides in the Knorr pyrrole synthesis [J].

Alberola, A ;

Ortega, AG ;

Sádaba, ML ;

Sañudo, C .

TETRAHEDRON, 1999, 55 (21) :6555-6566

[10] Chemoenzymatic synthesis of the polyketide macrolactone 10-deoxymethynolide [J].

Aldrich, CC ;

Venkatraman, L ;

Sherman, DH ;

Fecik, RA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (25) :8910-8911

← 1 2 3 4 5 6 7 8 9 10 →