Selective monosulfonylation of internal 1,2-diols catalyzed by di-n-butyltin oxide

Authors
Martinelli, MJ Vaidyanathan, R Van Khau, V
Citation
Mj. Martinelli et al., Selective monosulfonylation of internal 1,2-diols catalyzed by di-n-butyltin oxide, TETRAHEDR L, 41(20), 2000, pp. 3773-3776
Citations number
9
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
20
Year of publication
2000
Pages
3773 - 3776
Database
ISI
SICI code
0040-4039(20000521)41:20<3773:SMOI1C>2.0.ZU;2-2
Abstract
The reaction of internal 1,2-diols with catalytic n-Bu2SnO, p-TsCl (1.05 eq uiv.) and Et3N (1.1 equiv.) led to selective monotosylation. In the case of cyclic substrates, the cis-1,2-diol moiety appeared best suited for optima l results, supporting the intermediacy of a five-membered chelate. (C) 2000 Elsevier Science Ltd. All rights reserved.