The asymmetric hetero-Diels-Alder reaction of enamide aldehydes with Danishefsky's diene and an efficient synthesis of chiral binaphthyl ligands

被引：28

作者：

Gong, LZ ^{[1
]}

Pu, L ^{[1
]}

机构：

[1] Univ Virginia, Dept Chem, Charlottesville, VA 22901 USA

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 14期

关键词：

hetero-Diels-Alder reactions; asymmetric; catalysis; binaphthyl;

D O I：

10.1016/S0040-4039(00)00193-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

By varying the substituents on the nitrogen of enamide aldehydes, their reaction mode with Danishefsky's diene in the presence of Lewis acid catalysts can be controlled and the desired formal hetero-Diels-Alder products obtained. A new and efficient method to synthesize chiral binaphthyl ligands containing sterically bulky 3,3'-substitnents has been developed. Lewis acid complexes prepared from these binaphthyl ligands and AlMe3 are used to catalyze the hetero-Diels-Alder reaction of an enamide aldehyde with Danishefsky's diene with up to 78% ee. This catalytic asymmetric reaction may allow for the efficient synthesis of biologically interesting molecules such as fumonisins. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：2327 / 2331

页数：5

共 36 条

[1]

BEZUIDENHOUT CS, 1988, J CHEM SOC CHEM COMM, P743

[2]

Blackwell BA, 1996, ADV EXP MED BIOL, V392, P75

[3] A three-step procedure for asymmetric catalytic reductive amidation of ketones [J].

Burk, MJ ;

Casy, G ;

Johnson, NB .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (18) :6084-6085

[4] ENANTIOSELECTIVE MUKAIYAMA-ALDOL AND ALDOL-DIHYDROPYRONE ANNULATION REACTIONS CATALYZED BY A TRYPTOPHAN-DERIVED OXAZABOROLIDINE [J].

COREY, EJ ;

CYWIN, CL ;

ROPER, TD .

TETRAHEDRON LETTERS, 1992, 33 (46) :6907-6910

[5] EXPEDIENT ROUTE TO 3-SUBSTITUTED AND 3,3'-SUBSTITUTED 1,1'-BI-2-NAPHTHOLS BY DIRECTED ORTHO METALATION AND SUZUKI CROSS COUPLING METHODS [J].

COX, PJ ;

WANG, W ;

SNIECKUS, V .

TETRAHEDRON LETTERS, 1992, 33 (17) :2253-2256

[6] SILOXY DIENES IN TOTAL SYNTHESIS [J].

DANISHEFSKY, S .

ACCOUNTS OF CHEMICAL RESEARCH, 1981, 14 (12) :400-406

[7] USEFUL DIENE FOR DIELS-ALDER REACTION [J].

DANISHEFSKY, S ;

KITAHARA, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (25) :7807-7808

[8] TOTALLY SYNTHETIC ROUTES TO THE HIGHER MONOSACCHARIDES [J].

DANISHEFSKY, SJ ;

DENINNO, MP .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (01) :15-23

[9] ASYMMETRIC HETERO-DIELS-ALDER REACTION CATALYZED BY STABLE AND EASILY PREPARED CAB CATALYSTS [J].

GAO, QZ ;

MARUYAMA, T ;

MOURI, M ;

YAMAMOTO, H .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (07) :1951-1952

[10] Synthetic studies of antitumor macrolide laulimalide: Enantioselective synthesis of the C-3-C-14 segment by a catalytic hetero Diels-Alder strategy [J].

Ghosh, AK ;

Packiarajan, M ;

Cappiello, J .

TETRAHEDRON LETTERS, 1997, 38 (14) :2427-2430

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