Generation of homochiral aziridinium ion intermediates derived from 2,3-epoxy amines: Regiospecific nucleophilic trapping with nitrogen nucleophiles. Application in the synthesis of novel morpholinosphingolipid analogues with potential glucosylceramide synthase inhibitory activity
被引:29
作者:
Liu, QY
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机构:UNIV LEEDS, SCH CHEM, LEEDS LS2 9JT, W YORKSHIRE, ENGLAND
Liu, QY
Marchington, AP
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机构:UNIV LEEDS, SCH CHEM, LEEDS LS2 9JT, W YORKSHIRE, ENGLAND
Marchington, AP
Boden, N
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机构:UNIV LEEDS, SCH CHEM, LEEDS LS2 9JT, W YORKSHIRE, ENGLAND
Boden, N
Rayner, CM
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机构:UNIV LEEDS, SCH CHEM, LEEDS LS2 9JT, W YORKSHIRE, ENGLAND
Rayner, CM
机构:
[1] UNIV LEEDS, SCH CHEM, LEEDS LS2 9JT, W YORKSHIRE, ENGLAND
[2] UNIV LEEDS, CTR SELF ORG MOL SYST, LEEDS LS2 9JT, W YORKSHIRE, ENGLAND
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
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1997年
/
04期
关键词:
D O I:
10.1039/a604534k
中图分类号:
O62 [有机化学];
学科分类号:
070303 ;
081704 ;
摘要:
The Lewis acid induced rearrangement of 2,3-epoxy amines into the corresponding 2-trimethylsilyloxymethylaziridinium ions is described, Such intermediates have been characterised by H-1 NMR spectroscopy, and react with nitrogen nucleophiles regiospecifically to form 1-substituted 2,3-amino alcohols in good to excellent yields and with full stereochemical control, This methodology has been applied to the synthesis of a potential inhibitor of glucosylceramide synthase, a promising target for cancer chemotherapy.