Access to gamma-substituted (Z)-allylic borane reagents was achieved via a kinetically controlled hydroboration of various mono-substituted allenes with 10-TMS-9-borabicyclo[3.3.2]decane (Soderquist borane). A variety of synthetically useful structural motifs, including homoallylic alcohols and 1,5-diols,  were prepared in excellent diastereo- and enantioselectivities by reacting these gamma-substituted (Z)-allylic borane reagents with aldehydes. A review of theses methodology developments in conjunction with DFT studies and their application in natural product total synthesis will be presented.

Synthetic applications of gamma-substituted (Z)-allylic borane reagents

246th National Meeting (2013)

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