Reaction of alcohols (via the Mitsunobu-reaction) and alkyl halides with chiral selone derivatizing agents

Authors
Wu, RL Odom, JD Dunlap, RB Silks, LA
Citation
Rl. Wu et al., Reaction of alcohols (via the Mitsunobu-reaction) and alkyl halides with chiral selone derivatizing agents, TETRAHEDR-A, 10(8), 1999, pp. 1465-1470
Citations number
16
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
10
Issue
8
Year of publication
1999
Pages
1465 - 1470
Database
ISI
SICI code
0957-4166(19990423)10:8<1465:ROA(TM>2.0.ZU;2-H
Abstract
Coupling of a selone chiral derivatizing agent (CDA) to D,L-alkyl halides g ives Se-alkylated adducts in yields ranging from 76-97%. Reaction of D,L-al cohols with the selone CDAs via the Mitsunobu reaction has given rise to Se -alkylated adducts in yields ranging from 82-92%. Examination of the Se-77 NMR spectra of the resulting diastereomeric adducts indicates that discrimi nation of remotely disposed chiral centers is possible using this technique . (C) 1999 Elsevier Science Ltd. All rights reserved.