Useful enantioselective bicyclization reactions using an N-protonated chiral oxazaborolidine as catalyst

被引：64

作者：

Zhou, G ^{[1
]}

Hu, QY ^{[1
]}

Corey, EJ ^{[1
]}

机构：

[1] Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 21期

关键词：

D O I：

10.1021/ol035542a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Nine examples are reported of enantioselective [4 + 2] cycloaddition reactions of achiral, acyclic substrates to form chiral bicyclo[4.3.0]nonane or bicyclo[4.4.0]decane derivatives.

引用

页码：3979 / 3982

页数：4

共 15 条

[1] A DIELS-ALDER APPROACH TO STEMONA ALKALOIDS - TOTAL SYNTHESIS OF STENINE [J].

CHEN, CY ;

HART, DJ .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (15) :3840-3849

[2]

COREY EJ, 1955, J AM CHEM SOC, V77, P3667, DOI 10.1021/ja01618a082

[3]

Corey EJ, 2002, ANGEW CHEM INT EDIT, V41, P1650, DOI 10.1002/1521-3773(20020517)41:10<1650::AID-ANIE1650>3.0.CO

[4]

2-B

[5] The formyl C-H•••O hydrogen bond as a critical factor in enantioselective Lewis-acid catalyzed reactions of aldehydes [J].

Corey, EJ ;

Lee, TW .

CHEMICAL COMMUNICATIONS, 2001, (15) :1321-1329

[6] Asymmetric Diels-Alder reactions catalyzed by a triflic acid activated chiral oxazaborolidine [J].

Corey, EJ ;

Shibata, T ;

Lee, TW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (15) :3808-3809

[7] ASYMMETRIC DIELS-ALDER CYCLO-ADDITION REACTIONS WITH CHIRAL ALPHA, BETA-UNSATURATED N-ACYLOXAZOLIDINONES [J].

EVANS, DA ;

CHAPMAN, KT ;

BISAHA, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (04) :1238-1256

[8] Chiral C-2 symmetric Cu(II) complexes as catalysts for enantioselective intramolecular Diels-Alder reactions. Asymmetric synthesis of (-)-isopulo'upone [J].

Evans, DA ;

Johnson, JS .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (04) :786-787

[9] ASYMMETRIC INTRAMOLECULAR DIELS-ALDER REACTION CATALYZED BY CHIRAL ACYLOXYBORANE COMPLEX [J].

FURUTA, K ;

KANEMATSU, A ;

YAMAMOTO, H ;

TAKAOKA, S .

TETRAHEDRON LETTERS, 1989, 30 (51) :7231-7232

[10] A new powerful and practical BLA catalyst for highly enantioselective Diels-Alder reaction: An extreme acceleration of reaction rate by Bronsted acid [J].

Ishihara, K ;

Kurihara, H ;

Yamamoto, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (12) :3049-3050

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