Enantioselective Synthesis of Allenes by Reduction and a BrookRearrangement

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Enantioselective Meerwein-Ponndorf-Verley type reduction of alkynoylsilanes by a chiral lithium amide followed by a Brook rearrangement and SE2’ electrophilic substitution leads to the formation of enantiomerically enriched functionalized siloxyallenes in a one-pot process. In the case of enynoylsilanes, generated vinylallenes undergo in situ [4 + 2] cycloaddition to afford highly functionalized polycyclic compounds in excellent er’s, which show unusual facial selectivity.