STEREOSPECIFIC REDUCTION OF A BETA-KETO-NITRILE - FORMATION OF A SINGLE INDOLIC BETA-HYDROXY-NITRILE FROM A MIXTURE OF TAUTOMERS AND DIASTEREOISOMERS

被引：7

作者：

BAILEY, PD

HOLLINSHEAD, SP

MOORE, MH

MORGAN, KM

SMITHE, DI

VERNON, JM

机构：

[1] UNIV YORK,DEPT CHEM,YORK YO1 5DD,N YORKSHIRE,ENGLAND

[2] STERLING WINTHROP RES CTR,STERLING WINTHROP PHARMACEUT RES DIV,DEPT CHEM DEV,ALNWICK NE66 2JH,NORTHD,ENGLAND

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 21期

关键词：

D O I：

10.1016/S0040-4039(00)73246-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The beta-keto-nitrile 2, which is an advanced intermediate for the synthesis of several indole alkaloids, is composed of a mixture of enol/keto tautomers, and of diastereoisomers; nevertheless, reduction with sodium borohydride yields essentially a single diastereoisomer 3.

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页码：3585 / 3586

页数：2

相关论文

共 9 条

[1]

Bailey P., UNPUB

[2] DIASTEREOSELECTIVITY AND ENANTIOSELECTIVITY IN THE PICTET-SPENGLER REACTION [J].

BAILEY, PD ;

HOLLINSHEAD, SP ;

MCLAY, NR ;

MORGAN, K ;

PALMER, SJ ;

PRINCE, SN ;

REYNOLDS, CD ;

WOOD, SD .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (04) :431-439

[3] EXCEPTIONAL STEREOCHEMICAL CONTROL IN THE PICTET-SPENGLER REACTION [J].

BAILEY, PD ;

HOLLINSHEAD, SP ;

MCLAY, NR .

TETRAHEDRON LETTERS, 1987, 28 (43) :5177-5180

[4] USE OF THE KINETICALLY CONTROLLED PICTET-SPENGLER REACTION IN THE ASYMMETRIC-SYNTHESIS OF INDOLE ALKALOIDS - FORMAL SYNTHESES OF (-)-AJMALINE, (-)-KOUMINE, (-)-TABERPSYCHINE, (-)-KOUMIDINE AND (-)-SUAVOLINE [J].

BAILEY, PD ;

MCLAY, NR .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (04) :441-449

[5] GENERAL-APPROACH FOR THE SYNTHESIS OF AJMALINE-RELATED ALKALOIDS - ENANTIOSPECIFIC TOTAL SYNTHESIS OF (-)-SUAVEOLINE, (-)-RAUMACLINE, AND (-)-NB-METHYLRAUMACLINE [J].

FU, XY ;

COOK, JM .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (03) :661-672

[6]

HOLLINSHEAD SP, 1987, THESIS YORK

[7] STUDIES ON GELSEMIUM ALKALOIDS - TOTAL SYNTHESIS OF (+)-KOUMINE, (+)-TABERPSYCHINE, AND (+)-KOUMIDINE [J].

MAGNUS, P ;

MUGRAGE, B ;

DELUCA, MR ;

CAIN, GA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (13) :5220-5230

[8] SYNTHESIS OF AJMALINE [J].

MASAMUNE, S ;

ANG, SK ;

EGLI, C ;

NAKATSUKA, N ;

SARKAR, SK ;

YASUNARI, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (10) :2506-+

[9]

van Tamelen E. E., 1970, J AM CHEM SOC, V92, P2136