ASYMMETRIC-SYNTHESIS VIA ELECTROPHILE-MEDIATED CYCLIZATIONS

被引：61

作者：

FOX, DNA

GALLAGHER, T

机构：

[1] School of Chemistry, Bath University, Bath, Avon

来源：

TETRAHEDRON | 1990年 / 46卷 / 13-14期

关键词：

D O I：

10.1016/S0040-4020(01)85590-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The electrophile-mediated cyclisation of a series of allenic amines (8a-e), carrying a chiral benzylic residue on nitrogen, has been examined using Ag(I) and Pd(II). The cyclised products, (9/10)(using Ag(I)) and (12/13)(using Pd(II), CO, MeOH), are formed diastereoselectively. With Ag(I) up to 81% d.e. has been observed and the stereochemical course of this reaction has been established. The Pd(II)-mediated cyclisation is less selective (up to 43% d.e.) and the factors controlling the selectivities of both of these reactions are discussed. © 1990.

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页码：4697 / 4710

页数：14

相关论文

共 37 条

[1] CYCLIZATION OF GAMMA-ALLENIC AND DELTA-ALLENIC AMINES - SYNTHESIS OF 2-ALCENYL PYRROLIDINES AND 2-ALCENYL PIPERIDENES [J].

ARSENIYADIS, S ;

GORE, J .

TETRAHEDRON LETTERS, 1983, 24 (37) :3997-4000

[2] AN EFFICIENT SYNTHESIS OF (+/-)-PINIDINE [J].

ARSENIYADIS, S ;

SARTORETTI, J .

TETRAHEDRON LETTERS, 1985, 26 (06) :729-732

[3] ASYMMETRIC-SYNTHESIS WITH CHIRAL HYDROXYLAMINES - SYNTHESIS OF OPTICALLY PURE 4-SUBSTITUTED AZETIDINONES [J].

BALDWIN, SW ;

AUBE, J .

TETRAHEDRON LETTERS, 1987, 28 (02) :179-182

[4]

Bartlett P. A., 1984, ASYMMETRIC SYNTHESIS, V3, P411

[5] SELECTIVE BINDING OF ONE ENANTIOFACE OF MONOSUBSTITUTED ALKENES TO THE CHIRAL TRANSITION-METAL LEWIS ACID [(ETA-5-C5H5)RE(NO)(PPH3)]+ [J].

BODNER, GS ;

FERNANDEZ, JM ;

ARIF, AM ;

GLADYSZ, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (12) :4082-4084

[6] SYNTHESIS OF CHIRAL 1,2-DIAMINES [J].

BRUNI, E ;

CARDILLO, G ;

ORENA, M ;

SANDRI, S ;

TOMASINI, C .

TETRAHEDRON LETTERS, 1989, 30 (13) :1679-1682

[7] STEREOCONTROLLED REACTIONS THROUGH HETEROCYCLIC INTERMEDIATES [J].

CARDILLO, G ;

ORENA, M ;

SANDRI, S .

PURE AND APPLIED CHEMISTRY, 1988, 60 (11) :1679-1688

[8] ALLENES AND ACETYLENES .18. SYNTHESIS OF 3-PYRROLINES BY SILVER(I)-CATALYZED CYCLIZATION OF ALLENIC AMINES [J].

CLAESSON, A ;

SAHLBERG, C ;

LUTHMAN, K .

ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1979, 33 (04) :309-310

[9] ANNELATIVE RING EXPANSION VIA INTRAMOLECULAR [2 + 2] PHOTOCYCLOADDITION OF ALPHA,BETA-UNSATURATED GAMMA-LACTONES AND REDUCTIVE CLEAVAGE - SYNTHESIS OF HYDROCYCLOPENTACYCLOOCTENE-5-CARBOXYLATES [J].

COATES, RM ;

SENTER, PD ;

BAKER, WR .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (19) :3597-3607

[10]

DEPUE T, 1985, J AM CHEM SOC, V107, P2132

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