The enantioselective morita-baylis-hiliman reaction and its aza counterpart

被引：488

作者：

Masson, Geraldine ^{[1
]}

Housseman, Christopher ^{[1
]}

Zhu, Jieping ^{[1
]}

机构：

[1] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 25期

关键词：

asymmetric synthesis; Bronsted acids; Lewis bases; organocatalysis; reaction mechanisms;

D O I：

10.1002/anie.200604366

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The development of asymmetric Morita-Baylis-Hillman (MBH) reactions has evolved dramatically over the past few years, parallel to the emerging concept of bifunctional organocatalysis. Whereas organocatalysis is starting to compete with metal-based catalysis in several important organic transformations, the MBH reaction belongs to a group of prototypical reactions in which organocatalysis already display superiority over their metal-based counterparts. This Minireview summarizes recent mechanistic insights and advances in the design and synthesis of small organic molecules for enantioselective MBH and aza-MBH reactions. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：4614 / 4628

页数：15

共 182 条

[11] Theory of asymmetric organocatalysis of aldol and related reactions: Rationalizations and predictions [J].

Allemann, C ;

Gordillo, R ;

Clemente, FR ;

Cheong, PHY ;

Houk, KN .

ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (08) :558-569

[12] RATE ENHANCEMENT EFFECTS IN THE DABCO CATALYZED SYNTHESIS OF HYDROXYALKENOATE ESTERS [J].

AMEER, F ;

DREWES, SE ;

FREESE, S ;

KAYE, PT .

SYNTHETIC COMMUNICATIONS, 1988, 18 (05) :495-500

[13]

[Anonymous], 2006, ANGEW CHEM, V118, P1550

[14]

[Anonymous], 2002, MACROMOL CHEM PHYS

[15]

[Anonymous], 2004, METAL FREE ORGANIC C

[16]

[Anonymous], 2004, ANGEW CHEM, DOI DOI 10.1002/ANGE.200460059

[17] Dual catalyst control in the enantioselective intramolecular Morita-Baylis-Hillman reaction [J].

Aroyan, CE ;

Vasbinder, MM ;

Miller, SJ .

ORGANIC LETTERS, 2005, 7 (18) :3849-3851

[18] ACCELERATION IN WATER OF THE BAYLIS-HILLMAN REACTION [J].

AUGE, J ;

LUBIN, N ;

LUBINEAU, A .

TETRAHEDRON LETTERS, 1994, 35 (43) :7947-7948

[19] Quantum mechanical predictions of the stereoselectivities of proline-catalyzed asymmetric intermolecular aldol reactions [J].

Bahmanyar, S ;

Houk, KN ;

Martin, HJ ;

List, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (09) :2475-2479

[20] Transition states of amine-catalyzed aldol reactions involving enamine intermediates: Theoretical studies of mechanism, reactivity, and stereoselectivity [J].

Bahmanyar, S ;

Houk, KN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (45) :11273-11283

← 1 2 3 4 5 6 7 8 9 10 →