Enantioselective catalysis and complexity generation from allenoates

被引:566
作者
Cowen, Bryan J. [1 ]
Miller, Scott J. [1 ]
机构
[1] Yale Univ, Dept Chem, New Haven, CT 06520 USA
基金
美国国家科学基金会;
关键词
ASSISTED PHOSPHINE CATALYSIS; ELECTRON-DEFICIENT OLEFINS; ONE-POT SYNTHESIS; 3+2 CYCLOADDITION; ALLENIC ESTERS; 4+2 ANNULATION; FUNCTIONALIZED CYCLOPENTENES; ETHYL 2,3-BUTADIENOATE; NITROGEN-HETEROCYCLES; ASYMMETRIC-SYNTHESIS;
D O I
10.1039/b816700c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Lewis base catalysis of reactions with allenoates using phosphine and amine nucleophiles has emerged as a key platform for the generation of molecular complexity. Investigations in this area have established a range of suitable coupling partners for allenoates, including electron-deficient olefins, imines, and aldehydes. This tutorial review will describe these methodologies, with a special emphasis on recent work regarding asymmetric reactions using chiral Lewis base catalysts.
引用
收藏
页码:3102 / 3116
页数:15
相关论文
共 65 条
[31]   PPh3-Catalyzed Domino Reaction: A Facile Method for the Synthesis of Chroman Derivatives [J].
Meng, Xiangtai ;
Huang, You ;
Zhao, Hongxia ;
Xie, Peizhong ;
Ma, Jianze ;
Chen, Ruyu .
ORGANIC LETTERS, 2009, 11 (04) :991-994
[32]   Bifunctional Phosphine-Catalyzed Domino Reaction: Highly Stereoselective Synthesis of cis-2,3-Dihydrobenzofurans from Salicyl N-Thiophosphinyl Imines and Allenes [J].
Meng, Xiangtai ;
Huang, You ;
Chen, Ruyu .
ORGANIC LETTERS, 2009, 11 (01) :137-140
[33]   Phosphine triggered [3+2] allenoate-acrylate annulation: a mechanistic enlightenment [J].
Mercier, Evan ;
Fonovic, Branden ;
Henry, Chris ;
Kwon, Ohyun ;
Dudding, Travis .
TETRAHEDRON LETTERS, 2007, 48 (20) :3617-3620
[34]   Nucleophilic phosphine organocatalysis [J].
Methot, JL ;
Roush, WR .
ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (9-10) :1035-1050
[35]   The simplest "enzyme" [J].
Movassaghi, M ;
Jacobsen, EN .
SCIENCE, 2002, 298 (5600) :1904-1905
[36]   Enantioselective Binaphthophosphepine-Promoted [3+2] Annulations of N-Ts- and N-DPP-Imines with Allenoates and 2-Butynoates [J].
Pinto, Nathalie ;
Fleury-Bregeot, Nicolas ;
Marinetti, Angela .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (01) :146-151
[37]   Synthesis of novel conformationally restricted L-glutamate analogues [J].
Pyne, SG ;
Schafer, K ;
Skelton, BW ;
White, AH .
CHEMICAL COMMUNICATIONS, 1997, (23) :2267-2268
[38]   Totally Regio- and Stereoselective Behavior of Mono- and Diactivated Cyclic Alkenes in the Lu Reaction: Synthesis of Enantiopure Functionalized Cyclopentanes [J].
Ruano, Jose L. Garcia ;
Nunez, Alberto, Jr. ;
Martin, M. Rosario ;
Fraile, Alberto .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (23) :9366-9371
[39]   A promising new catalyst family for enantioselective cycloadditions involving allenes and imines:: chiral phosphines with transition metal-CH2-P:: linkages [J].
Scherer, Alexander ;
Gladysz, J. A. .
TETRAHEDRON LETTERS, 2006, 47 (36) :6335-6337
[40]   Target-oriented and diversity-oriented organic synthesis in drug discovery [J].
Schreiber, SL .
SCIENCE, 2000, 287 (5460) :1964-1969