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Synlett 2001; 2001(5): 0601-0604
DOI: 10.1055/s-2001-13358
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The Hydroboration of Propargyl Chloride: A Flexible One-pot Three-component Process Easily Directed Towards the Synthesis of (E)-Homoallylic Alcohols or anti-Homoallylic Alcohols

Marco Lombardo* , Stefano Morganti, Claudio Trombini
  • *Dipartimento di Chimica "G. Ciamician", Università di Bologna, via Selmi 2, I-40126 Bologna, Italy; Fax + 39(51)2 09 94 56; E-mail: marlom@ciam.unibo.it; trombini@ciam.unibo.it
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Publication Date:
31 December 2001 (online)

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The hydroboration of propargyl chloride by means of a dialkylborane affords 3-chloro-prop-1-en-1-yl boranes 6 which, in the presence of a quaternary ammonium chloride, rearrange into allylic boranes 9 and 10, precursors of (E)-homoallylic alcohols 7 or anti-homoallylic alcohols 5, respectively. Synthetic protocols for the selective generation of 5 and 7 were developed.

propargyl chloride - hydroboration - one-pot synthesis - (E)-homoallylic alcohols - anti-homoallylic alcohols