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

[31] N-Acyl-2-benzoxazolinones in titanium-mediated Aldol reactions [J].

Burlingame, MA ;

Mendoza, E ;

Ashley, GW .

TETRAHEDRON LETTERS, 2004, 45 (14) :2961-2964

[32] Synthesis of discodermolide intermediates from engineered polyketides [J].

Burlingame, MA ;

Mendoza, E ;

Ashley, GW ;

Myles, DC .

TETRAHEDRON LETTERS, 2006, 47 (07) :1209-1211

[33]

BURNELLCURTY C, 1993, SYNLETT, P131

[34] Synthesis of pyrroles with fused carbocycles or heterocycles from Weinreb N-vinyl-α-amino amides [J].

Calvo, L ;

González-Ortega, A ;

Navarro, R ;

Pérez, M ;

Sañudo, MC .

SYNTHESIS-STUTTGART, 2005, (18) :3152-3158

[35]

Campbell AD, 1998, SYNTHESIS-STUTTGART, P1707

[36] Catalytic, enantioselective synthesis of taranabant, a novel, acyclic cannabinoid-1 receptor inverse agonist for the treatment of obesity [J].

Chen, Cheng-yi ;

Frey, Lisa F. ;

Shultz, Scott ;

Wallace, Debra J. ;

Marcantonio, Karen ;

Payack, Joeseph F. ;

Vazquez, Enrique ;

Springfield, Shawn A. ;

Zhou, George ;

Liu, Ping ;

Kieczykowski, Gerard R. ;

Chen, Alex M. ;

Phenix, Brian D. ;

Singh, Utpal ;

Strine, Jeff ;

Izzo, Brianne ;

Krska, Shane W. .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2007, 11 (03) :616-623

[37] Solid phase synthesis of peptide hydroxamic acids [J].

Chen, JJ ;

Spatola, AF .

TETRAHEDRON LETTERS, 1997, 38 (09) :1511-1514

[38] Pyridone annulation by 4+2 coupling of dienolates with nitriles and nitrile equivalents. A solution to the acetonitrile problem [J].

Chen, YP ;

Li, TD ;

Sieburth, SM .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (20) :6826-6828

[39] Asymmetric synthesis of cyclic β-amino acids and cyclic amines via sequential diastereoselective conjugate addition and ring closing metathesis [J].

Chippindale, AM ;

Davies, SG ;

Iwamoto, K ;

Parkin, RM ;

Smethurst, CAP ;

Smith, AD ;

Rodriguez-Solla, H .

TETRAHEDRON, 2003, 59 (18) :3253-3265

[40] A facile one-pot synthesis of acyclic β-enamino ketones, an important class of versatile synthetic intermediates [J].

Choudhury, Anusuya ;

Breslav, Michael ;

Grimm, Jeffrey S. ;

Xiao, Tong ;

Xu, Dawei ;

Sorgi, Kirk L. .

TETRAHEDRON LETTERS, 2007, 48 (17) :3069-3072

← 1 2 3 4 5 6 7 8 9 10 →