NUCLEOPHILIC RING-OPENING OF CYCLIC SULPHAMIDITES

被引：22

作者：

GAUTUN, HSH ^{[1
]}

CARLSEN, PHJ ^{[1
]}

机构：

[1] UNIV TRONDHEIM,NORWEGIAN INST TECHNOL,ORGAN CHEM LAB,N-7034 TRONDHEIM,NORWAY

来源：

TETRAHEDRON-ASYMMETRY | 1995年 / 6卷 / 07期

关键词：

D O I：

10.1016/0957-4166(95)00211-7

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The cyclic sulphamidites (2S,4S)- and (2R,4S)-3-benzyl-4-benzyloxymethyl-2-oxo-1,2,3-oxathiazolidine 1 were prepared from S-glycidol in 60-66% overall yield. Nucleophilic ring opening of 1 by cyanide, azide and benzyloxy anions have been studied with respect to regio and stereospecificity. A mild procedure for benzylation of alcohols was introduced.

引用

页码：1667 / 1674

页数：8

共 26 条

[1] THE DIRECT SYNTHESIS OF THE CYCLIC SULPHAMIDATE OF (S)-PROLINOL - SIMULTANEOUS N-PROTECTION AND ACTIVATION TOWARDS NUCLEOPHILIC DISPLACEMENT OF OXYGEN
ALKER, D
DOYLE, KJ
HARWOOD, LM
MCGREGOR, A
[J]. TETRAHEDRON-ASYMMETRY, 1990, 1 (12) : 877 - 880
[2] ATAMI A, 1991, SYNT COMMUN, V21, P2383
[3] CYCLIC SULPHAMIDATES - NEW SYNTHETIC PRECURSORS FOR BETA-FUNCTIONALIZED ALPHA-AMINO-ACIDS
BALDWIN, JE
SPIVEY, AC
SCHOFIELD, CJ
[J]. TETRAHEDRON-ASYMMETRY, 1990, 1 (12) : 881 - 884
[4] NUCLEOPHILIC-ADDITION TO CYCLIC 1,2-SULFITES
CARLSEN, PHJ
AASE, K
[J]. ACTA CHEMICA SCANDINAVICA, 1993, 47 (06): : 617 - 619
[5] STEREOSELECTIVE SYNTHESIS OF (S)-PROPRANOLOL BY THE CYCLIC SULFITE ROUTE
CARLSEN, PHJ
AASE, K
[J]. ACTA CHEMICA SCANDINAVICA, 1993, 47 (07): : 737 - 738
[6] FACILE CONVERSION OF EPOXIDES TO BETA-HYDROXY NITRILES UNDER ANHYDROUS CONDITIONS WITH LITHIUM CYANIDE
CIACCIO, JA
STANESCU, C
BONTEMPS, J
[J]. TETRAHEDRON LETTERS, 1992, 33 (11) : 1431 - 1434
[7] Coppola GM, 1987, ASYMMETRIC SYNTHESIS
[8] ONE-POT STEREOSELECTIVE SYNTHESIS OF GLYCOSYL AZIDES VIA 1,2-CYCLIC SULFITE
ELMESLOUTI, A
BEAUPERE, D
DEMAILLY, G
UZAN, R
[J]. TETRAHEDRON LETTERS, 1994, 35 (23) : 3913 - 3916
[9] THE CHEMISTRY OF 2-OXAZOLINES (1985-PRESENT)
GANT, TG
MEYERS, AI
[J]. TETRAHEDRON, 1994, 50 (08) : 2297 - 2360
[10] A PRACTICAL SYNTHESIS OF D-MALATE ESTERS FROM L-TARTRATE ESTERS
GAO, Y
ZEPP, CM
[J]. TETRAHEDRON LETTERS, 1991, 32 (27) : 3155 - 3158

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