Reductive desulfurization using the Raney nickel sodium hypophosphite combination system without racemization of a secondary alcohol

被引：42

作者：

Nishide, K ^{[1
]}

Shigeta, Y ^{[1
]}

Obata, K ^{[1
]}

Inoue, T ^{[1
]}

Node, M ^{[1
]}

机构：

[1] KYOTO PHARMACEUT UNIV, KYOTO 607, JAPAN

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 13期

关键词：

D O I：

10.1016/0040-4039(96)00273-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Thioethers bearing an optically active secondary alcohol were desulfurized with Raney nickel - sodium hypophosphite - acetate buffer system to give optically active alcohols without racemization in high yields. This Raney nickel combination system exhibited a unique desulfurization of benzylthio or phenylthio group in the presence of benzyl ether.

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收藏

页码：2271 / 2274

页数：4

相关论文

共 21 条

[1]

BILLEK G, 1969, J LABELLED COMPD, V5, P3

[2] TRANSFORMATION OF SULFIDE LINKAGES TO CARBON-CARBON DOUBLE-BONDS - SYNTHESES OF [2.2]METAPARACYCLOPHANE-1,9-DIENES [J].

BOEKELHEIDE, V ;

ANDERSON, PH ;

HYLTON, TA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (05) :1558-1564

[3] THE SOURCE OF HYDROGEN IN REDUCTIVE DESULFURATION [J].

BONNER, WA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1952, 74 (04) :1033-1034

[4]

Caubere P., 1991, COMPREHENSIVE ORGANI, V8, P835

[5] CONFORMATIONAL ANALYSIS .9. EQUILIBRATIONS WITH RANEY NICKEL . CONFORMATIONAL ENERGY OF HYDROXYL GROUP AS A FUNCTION OF SOLVENT [J].

ELIEL, EL ;

SCHROETE.SH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (22) :5031-&

[6]

Greene T.W., 1991, PROTECTIVE GROUPS OR, V2nd

[7] ON THE SELECTIVITY OF DEPROTECTION OF BENZYL, MPM (4-METHOXYBENZYL) AND DMPM (3,4-DIMETHOXYBENZYL) PROTECTING GROUPS FOR HYDROXY FUNCTIONS [J].

HORITA, K ;

YOSHIOKA, T ;

TANAKA, T ;

OIKAWA, Y ;

YONEMITSU, O .

TETRAHEDRON, 1986, 42 (11) :3021-3028

[8] ONE-STEP SYNTHESIS OF THE ERYTHRINANE SKELETON BY ACID PROMOTED DOUBLE CYCLIZATION OF N-(CYCLOHEX-1-ENYL)-N-[2-(3,4-DIMETHOXYPHENYL)ETHYL]-ALPHA-(METHYLSULPHINYL)ACETAMIDE AND ITS DERIVATIVES [J].

ISHIBASHI, H ;

SATO, K ;

IKEDA, M ;

MAEDA, H ;

AKAI, S ;

TAMURA, Y .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (03) :605-609

[9] RADICAL CYCLIZATION OF N-(CYCLOHEX-2-ENYL)-ALPHA,ALPHA-DICHLOROACETAMIDES - STEREOSELECTIVE SYNTHESES OF (+/-)-MESEMBRANOL AND (+/-)-ELWESINE [J].

ISHIBASHI, H ;

SO, TS ;

OKOCHI, K ;

SATO, T ;

NAKAMURA, N ;

NAKATANI, H ;

IKEDA, M .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (01) :95-102

[10] NEW APPROACH TO STEREOSPECIFIC TOTAL SYNTHESIS OF RACEMIC CECROPIA JUVENILE-HORMONE [J].

KONDO, K ;

TUNEMOTO, D ;

MATSUI, K ;

MASAMUNE, S ;

NEGISHI, A .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1972, (23) :1311-&