THE DIRECT SYNTHESIS OF THE CYCLIC SULPHAMIDATE OF (S)-PROLINOL - SIMULTANEOUS N-PROTECTION AND ACTIVATION TOWARDS NUCLEOPHILIC DISPLACEMENT OF OXYGEN

被引：73

作者：

ALKER, D ^{[1
]}

DOYLE, KJ ^{[1
]}

HARWOOD, LM ^{[1
]}

MCGREGOR, A ^{[1
]}

机构：

[1] UNIV OXFORD,DYSON PERRINS LAB,OXFORD OX1 3QY,ENGLAND

来源：

TETRAHEDRON-ASYMMETRY | 1990年 / 1卷 / 12期

关键词：

D O I：

10.1016/S0957-4166(00)82278-8

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The preparation of the cyclic sulphamidate of (S)-prolinol has been achieved by reaction with sulphuryl chloride at low temperature. This material has been shown to be susceptible to acid catalysed nucleophilic attack to furnish 2-(N,N-dialkylamino)methyl- and 2-(methoxymethyl)pyrrolidines after hydrolysis of the intermediate sulphamic acid derivatives.

引用

页码：877 / 880

页数：4

共 16 条

[1] ASYMMETRIC TRANSFORMATION OF SYMMETRICAL EPOXIDES TO ALLYLIC ALCOHOLS BY LITHIUM (S)-2-(N,N-DISUBSTITUTED AMINOMETHYL)PYRROLIDIDE
ASAMI, M
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1990, 63 (03) : 721 - 727
[2] A NOVEL ASYMMETRIC-SYNTHESIS OF CHIRAL CYCLOPENTANOID BUILDING-BLOCKS BY THE USE OF CHIRAL LITHIUM AMIDE
ASAMI, M
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1990, 63 (05) : 1402 - 1408
[3] AN ASYMMETRIC TRANSFORMATION OF CYCLOHEXENE OXIDE TO (S)-2-CYCLOHEXEN-1-OL BY CHIRAL LITHIUM AMIDES
ASAMI, M
[J]. CHEMISTRY LETTERS, 1984, (05) : 829 - 832
[4] BALDWIN JE, TETRAHEDRON ASYMMETR
[5] CYCLIC SULFAMIDITE ANALOGS OF PENICILLANIC ACID
CUTHBERT, BK
LOWE, G
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (22) : 1702 - 1703
[6] 1,2,3-OXATHIAZOLIDINES - A NEW HETEROCYCLIC SYSTEM
DEYRUP, JA
MOYER, CL
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (01) : 175 - &
[7] PREPARATION OF PROLINE DERIVED LITHIUM AMIDE BASES AND THEIR USE IN ENANTIOSELECTIVE DEPROTONATION OF MESO EPOXIDES
HENDRIE, SK
LEONARD, J
[J]. TETRAHEDRON, 1987, 43 (14) : 3289 - 3294
[8] FLUORIDE-INDUCED FORMATION AND RING-OPENING OF CYCLIC SULFAMATES FROM HYDROXY TRIFLAMIDES - SYNTHETIC AND MECHANISTIC STUDIES
LYLE, TA
MAGILL, CA
PITZENBERGER, SM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (25) : 7890 - 7891
[9] ASYMMETRIC-SYNTHESIS BASED ON CHIRAL DIAMINES HAVING PYRROLIDINE RING
MUKAIYAMA, T
[J]. TETRAHEDRON, 1981, 37 (23) : 4111 - 4119
[10] ASYMMETRIC REDUCTION OF PROCHIRAL KETO ESTERS WITH A CHIRAL REDUCING AGENT PREPARED FROM TIN(II) CHLORIDE, CHIRAL DIAMINE, AND DIISOBUTYLALUMINUM HYDRIDE
MUKAIYAMA, T
TOMIMORI, K
ORIYAMA, T
[J]. CHEMISTRY LETTERS, 1985, (06) : 813 - 816

← 1 2 →