Discrimination of diastereotopic sulfonyl oxygens by intramolecular hydrogen bonding: Stereoselective hydrogenation of alpha-sulfonyl radicals

Authors
Mase, N Watanabe, Y Toru, T
Citation
N. Mase et al., Discrimination of diastereotopic sulfonyl oxygens by intramolecular hydrogen bonding: Stereoselective hydrogenation of alpha-sulfonyl radicals, TETRAHEDR L, 40(14), 1999, pp. 2797-2800
Citations number
11
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
14
Year of publication
1999
Pages
2797 - 2800
Database
ISI
SICI code
0040-4039(19990402)40:14<2797:DODSOB>2.0.ZU;2-6
Abstract
Stereoselective intramolecular hydrogen bonding between the hydroxy group a nd a stereogenic sulfonyl oxygen led to high diastereoselectivity in the ra dical reaction of alpha-(1-hydroxyethyl)vinyl sulfone with alkyl iodides an d tributyltin hydride in the presence of triethylborane as a radical initia tor. Intramolecular hydrogen bonding was demonstrated to play an important role in controlling the diastereoselectivity. (C) 1999 Elsevier Science Ltd . All rights reserved.