Literature DB >> 21410173

Enantioselective syntheses of syn- and anti-β-hydroxyallylsilanes via allene hydroboration-aldehyde allylboration reactions.

Ming Chen1, William R Roush.   

Abstract

The kinetic hydroboration of allenylsilane 5 with ((d)Ipc)(2)BH at -40 °C provides allylborane 9Z with ≥12:1 selectivity. When the hydroboration is performed at temperatures above -40 °C, 9Z isomerizes to the thermodynamically more stable allylborane 9E with >20:1 selectivity. Subsequent treatment of 9Z or 9E with aldehydes at -78 °C provides syn- or anti-β-hydroxyallylsilanes, 7 or 8, respectively.
© 2011 American Chemical Society

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Year:  2011        PMID： 21410173      PMCID： PMC3075570          DOI： 10.1021/ol200392u

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


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