LEWIS-ACID INDUCED REARRANGEMENT OF 2,3-EPOXY AMINES AND REGIOSPECIFIC NUCLEOPHILIC TRAPPING OF AZIRIDINIUM ION INTERMEDIATES WITH AMINO-ACID ESTERS - SYNTHESIS OF N(2-AMINO-3-HYDROXYALKYL)-SUBSTITUTED AMINO-ACID ESTERS

Authors
LIU QY MARCHINGTON AP BODEN N RAYNER CM
Citation
Qy. Liu et al., LEWIS-ACID INDUCED REARRANGEMENT OF 2,3-EPOXY AMINES AND REGIOSPECIFIC NUCLEOPHILIC TRAPPING OF AZIRIDINIUM ION INTERMEDIATES WITH AMINO-ACID ESTERS - SYNTHESIS OF N(2-AMINO-3-HYDROXYALKYL)-SUBSTITUTED AMINO-ACID ESTERS, Synlett, (10), 1995, pp. 1037
Citations number
31
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synlett → ACNP
ISSN journal
09365214
Issue
10
Year of publication
1995
Database
ISI
SICI code
0936-5214(1995):10<1037:LIRO2A>2.0.ZU;2-9
Abstract
Rearrangement of homochiral 2,3-epoxy amines by treatment with TMSOTf gives 3-trimethylsilyloxy-1,2-aziridinium triflates, which undergo eff icient regiospecific ring opening at C-1 with amino acid ester nucleop hiles to give N-(2-amino-3-hydroxyalkyl)-substituted amino acid esters .