SYNTHESIS AND CONFIGURATIONAL ASSIGNMENT OF SOME NOVEL BICYCLIC SULPHAMIDITES AND SULPHAMIDATES

被引:21
作者
LOWE, G
REED, MA
机构
[1] The Dyson Perrins Laboratory, Oxford University, Oxford, OX1 3QY, South Parks Road
关键词
D O I
10.1016/S0957-4166(00)82280-6
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
(S)-Prolinol and 2(RS)-piperidine-methanol each react with thionyl chloride to give a pair of diastereoisomeric bicyclic sulphamidites which differ only in their configuration at sulphur. By contrast 2(RS)-pyrrolidine-ethanol and 2(RS)-piperidine-ethanol each react with thionyl chloride to give single diastereoisomeric products. The configurations of these bicyclic sulphamidites, and the sulphamidates derived from them, have been determined.
引用
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页码:885 / 894
页数:10
相关论文
共 19 条
[1]  
ALKER D, IN PRESS TETRAHEDRON
[2]  
ALTONA C, 1966, RECL TRAV CHIM PAY-B, V85, P1197
[3]  
BALDWIN JE, IN PRESS TETRAHEDRON
[4]  
COWLING PW, UNPUB
[5]   ACID-CATALYZED HYDROLYSIS OF AMIDOSULFITES [J].
COX, S ;
ELDUSOUQUI, OMH ;
MCCORMACK, W ;
TILLETT, JG .
JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (07) :949-950
[6]   CYCLIC SULFAMIDITE ANALOGS OF PENICILLANIC ACID [J].
CUTHBERT, BK ;
LOWE, G .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (22) :1702-1703
[7]  
CUTHBERT BK, 1985, THESIS OXFORD
[8]   1,2,3-OXATHIAZOLIDINES - A NEW HETEROCYCLIC SYSTEM [J].
DEYRUP, JA ;
MOYER, CL .
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (01) :175-&
[9]   VICINAL DIOL CYCLIC SULFATES - LIKE EPOXIDES ONLY MORE REACTIVE [J].
GAO, Y ;
SHARPLESS, KB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (22) :7538-7539
[10]   CYCLIC SULFATES CONTAINING ACID-SENSITIVE GROUPS AND CHEMOSELECTIVE HYDROLYSIS OF SULFATE ESTERS [J].
KIM, BM ;
SHARPLESS, KB .
TETRAHEDRON LETTERS, 1989, 30 (06) :655-658