The hydroboration of propargyl chloride: A flexible one-pot three-component process easily directed towards the synthesis of (E)-homoallylic alcoholsor anti-homoallylic alcohols

Authors
Lombardo, M Morganti, S Trombini, C
Citation
M. Lombardo et al., The hydroboration of propargyl chloride: A flexible one-pot three-component process easily directed towards the synthesis of (E)-homoallylic alcoholsor anti-homoallylic alcohols, SYNLETT, (5), 2001, pp. 601-604
Citations number
7
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNLETT
ISSN journal
09365214 → ACNP
Issue
5
Year of publication
2001
Pages
601 - 604
Database
ISI
SICI code
0936-5214(200105):5<601:THOPCA>2.0.ZU;2-#
Abstract
The hydroboration of propargyl chloride by means of a dialkylborane affords 3-chloro-prop-l-en-l-yl boranes 6 which, in the presence of a quaternary a mmonium chloride, rearrange into allylic boranes 9 and 10, precursors of (E )-homoallylic alcohols 7 or anti-homoallylic alcohols 5, respectively. Synt hetic protocols for the selective generation of 5 and 7 were developed.