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Synfacts 2005(0): 0072-0072  
DOI: 10.1055/s-2005-869931
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Novel Asymmetric Synthesis of Homopropar­-gylic Alcohols via Allenylboration

Contributor(s): Paul Knochel, Andrei Gavryushin
C. Lai, J. A. Soderquist*
University of Puerto Rico, Puerto Rico
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Publikationsdatum:
20. Juli 2005 (online)

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Significance

Non-racemic homopropargylic alcohols are important intermediates for the synthesis of different classes of useful compounds. This approach offers the use of readily accessible and recoverable chiral auxiliary, along with excellent selectivity and simplicity of the whole process. Allenylmagnesium bromide serves as a convenient C3-chain source without the need of using tin or silicon intermediates.