STEREOCONTROLLED FORMATION OF CIS AND TRANS RING JUNCTIONS IN HYDRINDANE AND DECALIN SYSTEMS BY PALLADIUM-CATALYZED REGIOSELECTIVE AND STEREOSPECIFIC HYDROGENOLYSIS OF ALLYLIC FORMATES

被引：86

作者：

MANDAI, T

MATSUMOTO, T

KAWADA, M

TSUJI, J

机构：

[1] Department of Applied Chemistry, Faculty of Engineering, Okayama University of Science, Okayama 700, Ridai-cho

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 05期

关键词：

D O I：

10.1021/jo00031a005

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Both cis and trans ring junctions can be generated selectively in hydrindane, decalin, and steroid systems by the palladium-catalyzed regioselective and stereospecific hydrogenolysis of allylic formates.

引用

页码：1326 / 1327

页数：2

共 8 条

[1] HYDROBORATION .5. NEW SYNTHESIS OF ANDROSTERONE + 19-NORANDROSTERONE [J].

CAGLIOTI, L ;

MAINA, G ;

SELVA, A ;

CAINELLI, G .

TETRAHEDRON, 1964, 20 (04) :957-&

[2]

KABALKA GW, 1988, ORG SYNTH, V6, P293

[3] STEREOSPECIFIC REDUCTIVE METHYLATION VIA A RADICAL CYCLIZATION DESILYLATION PROCESS [J].

STORK, G ;

SOFIA, MJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (21) :6826-6828

[4] CONTROL OF RING JUNCTION STEREOCHEMISTRY VIA RADICAL CYCLIZATION [J].

STORK, G ;

KAHN, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (02) :500-501

[5] ALLYLIC SUBSTITUTIONS WITH RETENTION OF STEREOCHEMISTRY [J].

TROST, BM ;

VERHOEVEN, TR .

JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (19) :3215-3216

[6] ALLYLIC ALKYLATION - PALLADIUM-CATALYZED SUBSTITUTIONS OF ALLYLIC CARBOXYLATES - STEREOCHEMISTRY AND REGIOCHEMISTRY [J].

TROST, BM ;

VERHOEVEN, TR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (14) :4730-4743

[7]

TSUJI J, 1979, TETRAHEDRON LETT, P613

[8] REGIOSELECTIVE SYNTHESIS OF 1-OLEFINS BY PALLADIUM-CATALYZED HYDROGENOLYSIS OF TERMINAL ALLYLIC COMPOUNDS WITH AMMONIUM FORMATE [J].

TSUJI, J ;

SHIMIZU, I ;

MINAMI, I .

CHEMISTRY LETTERS, 1984, (06) :1017-1020

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