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Stereoselective Allylic C-H Activation with Tertiary Alkylboranes: A New Method for Preparing Cycloalkyl Derivatives with Three Adjacent Stereocenters.

A regio- and stereoselective migration takes place under mild conditions for tertiary organoboranes obtained by hydroboration of tetrasubstituted cyclic alkenes. A subsequent amination proceeds with perfect control of the stereochemistry. The scheme shows an example of this for the reaction of bicyclo[4.3.0]non-1(6)-ene (1) to 2 via intermediates 3 and 4. Compound 2 is formed as the single diastereomer in 69% yield.