Regio- and stereoselective construction of γ-butenolides through phosphine-catalyzed substitution of Morita-Baylis-Hillman acetates:: An organocatalytic allylic alkylation

被引：182

作者：

Cho, CW ^{[1
]}

Krische, MJ ^{[1
]}

机构：

[1] Univ Texas, Dept Chem & Biochem, Austin, TX 78712 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2004年 / 43卷 / 48期

关键词：

D O I：

10.1002/anie.200461381

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Hold the metal: Upon exposure of acetates 1 to substoichiometric quantities of triphenylphosphane in the presence of 2, regioselective metal-free allylic substitution occurs through a formal tandem SN2′-S N2′ substitution mechanism to provide γ-butenolides 3 with high levels of regio- and diastereocontrol (see scheme).

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页码：6689 / 6691

页数：3

相关论文

共 24 条

[1] Catalytic crossed Michael cycloisomerization of thioenoates:: Total synthesis of (±)-ricciocarpin A [J].

Agapiou, K ;

Krische, MJ .

ORGANIC LETTERS, 2003, 5 (10) :1737-1740

[2] Annonaceous acetogenins: Recent progress [J].

Alali, FQ ;

Liu, XX ;

McLaughlin, JL .

JOURNAL OF NATURAL PRODUCTS, 1999, 62 (03) :504-540

[3] Applications of Baylis-Hillman chemistry: enantioselective synthesis of (-)-methyl 3-aryl-2-methylene-3-(prop-2-yn-1-yloxy)propanoates via chiral leaving group strategy [J].

Basavaiah, D ;

Kumaragurubaran, N ;

Sharada, DS ;

Reddy, RM .

TETRAHEDRON, 2001, 57 (38) :8167-8172

[4] The first enantioselective organocatalytic Mukaiyama- Michael reaction:: A direct method for the synthesis of enantioenriched γ-butenolide architecture [J].

Brown, SP ;

Goodwin, NC ;

MacMillan, DWC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (05) :1192-1194

[5] The synthesis of γ-alkylidenebutenolides [J].

Brückner, R .

CURRENT ORGANIC CHEMISTRY, 2001, 5 (06) :679-718

[6] Vinylogous Mannich reactions: selectivity and synthetic utility [J].

Bur, SK ;

Martin, SF .

TETRAHEDRON, 2001, 57 (16) :3221-3242

[7] The vinylogous aldol reaction: A valuable, yet understated carbon-carbon bond-forming maneuver [J].

Casiraghi, G ;

Zanardi, F ;

Appendino, G ;

Rassu, G .

CHEMICAL REVIEWS, 2000, 100 (06) :1929-1972

[8] Phosphine-catalyzed regiospecific allylic amination and dynamic kinetic resolution of Morita-Baylis-Hillman acetates [J].

Cho, CW ;

Kong, JR ;

Krische, MJ .

ORGANIC LETTERS, 2004, 6 (08) :1337-1339

[9]

Christoffers J, 2001, SYNLETT, P723

[10] REACTIVITY OF PENTACOORDINATE AND HEXACOORDINATE SILICON-COMPOUNDS AND THEIR ROLE AS REACTION INTERMEDIATES [J].

CHUIT, C ;

CORRIU, RJP ;

REYE, C ;

YOUNG, JC .

CHEMICAL REVIEWS, 1993, 93 (04) :1371-1448