ENANTIOSELECTIVITY IN THE RITTER-TYPE SUBSTITUTION-REACTION VIA EPISULFONIUM ION - RETENTION OF CONFIGURATION

被引:28
作者
TOSHIMITSU, A
HIROSAWA, C
TANIMOTO, S
机构
[1] Institute for Chemical Research, Kyoto University, Uji, Kyoto
关键词
AMIDOSULFENILATION; ENANTIOSELECTIVITY; EPISULFONIUM ION; RITTER-TYPE REACTION;
D O I
10.1016/S0040-4039(00)92159-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Ritter-type substitution reaction of optically active beta-hydroxyalkyl phenyl sulfides was found to proceed with retention of configuration through the participation of phenylthio group to afford optically active amides.
引用
收藏
页码:4317 / 4320
页数:4
相关论文
共 38 条
[1]   ALKENE CARBOSULFENYLATION AND CARBOSELENYLATION - THE USE OF ALLYLTRIMETHYLSILANE AND O-SILYLATED ENOLATES [J].
ALEXANDER, RP ;
PATERSON, I .
TETRAHEDRON LETTERS, 1983, 24 (52) :5911-5914
[2]   STUDY OF THE REDUCTIVE CLEAVAGE OF SELENIDES WITH NICKEL BORIDE - A CONVENIENT DESELENIZATION PROCEDURE [J].
BACK, TG ;
BIRSS, VI ;
EDWARDS, M ;
KRISHNA, MV .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (16) :3815-3822
[3]   ANODIC ACETAMIDOSULFENYLATION OF ALKENES [J].
BEWICK, A ;
COE, DE ;
MELLOR, JM ;
WALTON, DJ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1980, (02) :51-52
[5]   THIOAMMONIUM IONS - AZASULFENYLATION REACTIONS [J].
CASERIO, MC ;
KIM, JK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (11) :3231-3233
[6]   SYNTHESIS OF VINYL SULFIDES, AZIDO SULFIDES, AND OLEFINS FROM BETA-HYDROXY-SULFIDES [J].
DUMONT, W ;
KRIEF, A .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1980, (14) :673-675
[7]   ON THE DIRECT FORMATION OF EPISULFONIUM IONS FROM ALKENES - AN APPLICATION TO THE SYNTHESIS OF HIGHER-ORDER CARBOCYCLES VIA EPISULFONIUM ION INITIATED POLYENE CYCLIZATIONS [J].
EDSTROM, ED ;
LIVINGHOUSE, T .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (05) :949-951
[8]   NEW METHODS FOR THE GENERATION OF EPISULFONIUM IONS - AN APPLICATION TO THE SYNTHESIS OF CARBOCYCLES VIA SULFENIUM ION PROMOTED ARENE ALKENE CYCLIZATIONS [J].
EDSTROM, ED ;
LIVINGHOUSE, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (06) :1334-1336
[9]  
FUJISAWA T, 1985, TETRAHEDRON LETT, V26, P77