SILVER(I) CATALYZED AMINO CYCLIZATION OF O-(2,3-BUTADIENYL) CARBAMATES - AN EFFICIENT AND STEREOSELECTIVE SYNTHESIS OF 4-VINYL-2-OXAZOLIDINONES

被引：33

作者：

KIMURA, M ^{[1
]}

FUGAMI, K ^{[1
]}

TANAKA, S ^{[1
]}

TAMARU, Y ^{[1
]}

机构：

[1] NAGASAKI UNIV,FAC ENGN,DEPT APPL CHEM,BUNKYO KU,NAGASAKI 852,JAPAN

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 44期

关键词：

D O I：

10.1016/0040-4039(91)80169-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Silver(I) salts catalyze an amino cyclization of O-(2,3-butadienyl) N-tosyl-carbamates to provide mixtures of cis and trans-5-substituted N-tosyl-4-vinyl-2-oxazolidinones, the trans-isomers predominantly or exclusively.

引用

页码：6359 / 6362

页数：4

共 19 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] PREPARATION OF ALPHA-ALKENYL-2-TETRAHYDROPYRANES BY WAY OF THE CYCLIZATION OF DELTA-ALLENIC ALCOHOLS [J].

AUDIN, P ;

DOUTHEAU, A ;

GORE, J .

TETRAHEDRON LETTERS, 1982, 23 (42) :4337-4340

[3] A HIGHLY STEREOSELECTIVE CONVERSION OF ALPHA-ALLENIC ALCOHOLS TO 1,2-SYN AMINO ALCOHOL DERIVATIVES VIA IODOCARBAMATION [J].

FRIESEN, RW .

TETRAHEDRON LETTERS, 1990, 31 (30) :4249-4252

[4] SYNTHESES OF "2,3,6-TRIDEOXY-3-AMINO-NITROHEXOSES AND 2,3,6-TRIDEOXY-3-NITROHEXOSES [J].

HAUSER, FM ;

ELLENBERGER, SR .

CHEMICAL REVIEWS, 1986, 86 (01) :35-67

[5] ASYMMETRIC CYCLIZATION OF 2-BUTENYLENE DICARBAMATES CATALYZED BY CHIRAL FERROCENYLPHOSPHINE-PALLADIUM COMPLEXES - CATALYTIC ASYMMETRIC-SYNTHESIS OF OPTICALLY-ACTIVE 2-AMINO-3-BUTENOLS [J].

HAYASHI, T ;

YAMAMOTO, A ;

ITO, Y .

TETRAHEDRON LETTERS, 1988, 29 (01) :99-102

[6] ENANTIOSELECTIVE TOTAL SYNTHESIS OF (+)-NEGAMYCIN AND (-)-EPINEGAMYCIN BY AN ASYMMETRIC 1,3-DIPOLAR CYCLOADDITION [J].

IIDA, H ;

KASAHARA, K ;

KIBAYASHI, C .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (15) :4647-4648

[7] CONFORMATIONAL-ANALYSIS OF 3-BUTEN-2-OL - A MODEL ASYMMETRIC OLEFIN [J].

KAHN, SD ;

HEHRE, WJ .

TETRAHEDRON LETTERS, 1985, 26 (31) :3647-3650

[8] MODELING CHEMICAL-REACTIVITY .6. COMPARISON OF CONFORMATIONAL ENERGY PROFILES AND ELECTROPHILIC REACTIVITIES AND STEREOSELECTIVITIES OF CHIRAL ALLYLIC ALCOHOLS AND ETHERS - EVIDENCE AGAINST INTRAMOLECULAR HYDROGEN-BONDING IN ALLYLIC ALCOHOLS [J].

KAHN, SD ;

HEHRE, WJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (03) :666-671

[9] CONVENIENT SYNTHESIS OF DENSELY FUNCTIONALIZED N-SUBSTITUTED 4-METHYLENE-2-OXAZOLIDINONE [J].

KIMURA, M ;

KURE, S ;

YOSHIDA, Z ;

TANAKA, S ;

FUGAMI, K ;

TAMARU, Y .

TETRAHEDRON LETTERS, 1990, 31 (34) :4887-4890

[10] PALLADIUM(II)-MEDIATED ROUTES TO FUNCTIONALIZED HETEROCYCLES [J].

LATHBURY, D ;

VERNON, P ;

GALLAGHER, T .

TETRAHEDRON LETTERS, 1986, 27 (49) :6009-6012

← 1 2 →