Enantioselective α-heterofunctionalisation of carbonyl compounds:: organocatalysis is the simplest approach

被引：277

作者：

Guillena, Gabriela ^{[1
]}

Ramon, Diego J. ^{[1
]}

机构：

[1] Univ Alicante, ISO, Dept Quim Organ, Fac Ciencias, E-03080 Alicante, Spain

来源：

TETRAHEDRON-ASYMMETRY | 2006年 / 17卷 / 10期

关键词：

D O I：

10.1016/j.tetasy.2006.05.020

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Enantioselective organocatalytic processes have reached maturity in recent years with an impressive number of applications now available. The application of these advantageous methodologies to the construction of chiral alpha-hetereofunctionalised carbonyl compounds allows us to obtain important chiral building blocks, such as a-amino acids, alpha-amino alcohols, aziridines, epoxides, 1,2-diols and alpha-sulfenylated, selenenylated and halogenated carbonyl derivatives. Proline, imidazolidinone derivatives, cinchona alkaloids and their ammonium salts, as well as Bronsted acid derivatives, have been used as chiral catalysts for these purposes. A survey of contributions in this field will be discussed throughout this review. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：1465 / 1492

页数：28

共 246 条

[1] Organocatalytic asymmetric hydroxylation of β-keto esters:: Metal-free synthesis of optically active anti-diols [J].

Acocella, MR ;

Mancheño, OG ;

Bella, M ;

Jorgensen, KA .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (23) :8165-8167

[2] Asymmetric Weitz-Scheffer epoxidation of isoflavones with hydroperoxides mediated by optically active phase-transfer catalysts [J].

Adam, W ;

Rao, PB ;

Degen, HG ;

Levai, A ;

Patonay, T ;

Saha-Möller, CR .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (01) :259-264

[3] Asymmetric Weitz-Scheffer epoxidation of conformationally flexible and fixed enones with sterically demanding hydroperoxides mediated by optically active phase-transfer catalysts [J].

Adam, W ;

Rao, PB ;

Degen, HG ;

Saha-Möller, CR .

TETRAHEDRON-ASYMMETRY, 2001, 12 (01) :121-125

[4] Synthesis of optically active α-hydroxy ketones by enantioselective oxidation of silyl enol ethers with a fructose-derived dioxirane [J].

Adam, W ;

Fell, RT ;

Saha-Möller, CR ;

Zhao, CG .

TETRAHEDRON-ASYMMETRY, 1998, 9 (03) :397-401

[5] Catalytic, asymmetric sulfur ylide-mediated epoxidation of carbonyl compounds: Scope, selectivity, and applications in synthesis [J].

Aggarwal, VK ;

Winn, CL .

ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (08) :611-620

[6] Asymmetric synthesis of N-aryl aziridines [J].

Aires-de-Sousa, J ;

Prabhakar, S ;

Lobo, AM ;

Rosa, AM ;

Gomes, MJS ;

Corvo, MC ;

Williams, DJ ;

White, AJP .

TETRAHEDRON-ASYMMETRY, 2002, 12 (24) :3349-3365

[7] A new enantioselective synthesis of N-arylaziridines by phase-transfer catalysis [J].

AiresdeSousa, J ;

Lobo, AM ;

Prabhakar, S .

TETRAHEDRON LETTERS, 1996, 37 (18) :3183-3186

[8] Manumycin A: Synthesis of the (+)-enantiomer and revision of stereochemical assignment [J].

Alcaraz, L ;

Macdonald, G ;

Ragot, JP ;

Lewis, N ;

Taylor, RJK .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (11) :3526-3527

[9] Synthesis and applications of C2-symmetric guanidine bases [J].

Allingham, MT ;

Howard-Jones, A ;

Murphy, PJ ;

Thomas, DA ;

Caulkett, PWR .

TETRAHEDRON LETTERS, 2003, 44 (48) :8677-8680

[10]

Anstiss M, 2003, SYNLETT, P1213

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