NUCLEOPHILIC RING-OPENING OF CYCLIC 1,2-SULFITES WITH NITROGEN NUCLEOPHILES - A ROUTE TO ENANTIOPURE BENZYLIC AMINO-ALCOHOLS

Authors
NYMANN K MYLVAGANAM S SVENDSEN JS
Citation
K. Nymann et al., NUCLEOPHILIC RING-OPENING OF CYCLIC 1,2-SULFITES WITH NITROGEN NUCLEOPHILES - A ROUTE TO ENANTIOPURE BENZYLIC AMINO-ALCOHOLS, Acta chemica Scandinavica, 52(8), 1998, pp. 1060-1063
Citations number
15
Categorie Soggetti
Chemistry,Biology
Journal title
Acta chemica Scandinavica → ACNP
ISSN journal
0904213X
Volume
52
Issue
8
Year of publication
1998
Pages
1060 - 1063
Database
ISI
SICI code
0904-213X(1998)52:8<1060:NROC1W>2.0.ZU;2-N
Abstract
The reaction between cyclic 1,2-sulfites and two imide and two sulfona mide nucleophiles has been Investigated in order to develop a procedur e for the enantioselective preparation of N-protected vicinal amino al cohols. The results show that both imide and sulfonamide anions react with cyclic sulfites, yielding the desired products. In some cases the regioselectivities are low, and for the sulfonamides products origina ting from nucleophilic addition to the sulfite sulfur are observed.