Stereoselective synthesis of alpha,alpha-disubstituted amines by a sequential nucleophilic addition to O-protected cyanohydrins

Authors
Charette, AB Gagnon, A
Citation
Ab. Charette et A. Gagnon, Stereoselective synthesis of alpha,alpha-disubstituted amines by a sequential nucleophilic addition to O-protected cyanohydrins, TETRAHEDR-A, 10(10), 1999, pp. 1961-1968
Citations number
36
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
10
Issue
10
Year of publication
1999
Pages
1961 - 1968
Database
ISI
SICI code
0957-4166(19990521)10:10<1961:SSOAAB>2.0.ZU;2-F
Abstract
The first enantioselective double nucleophilic addition reaction to O-prote cted cyanohydrin was achieved in 71% yield and 82:18 enantiomeric ratio by using a bis(BINOL)titanium Lewis acid complex. New (4S,5S)-2,2-dialkyl-4,5- bis(hydroxymethyl)-1,3-dioxolane titanium complexes were synthesized and th ey displayed good levels of enantioselection in the nucleophilic addition r eaction. (C) 1999 Elsevier Science Ltd. All rights reserved.