Synthesis of enantioenriched tertiary benzylic alcohols via stereospecific lithiation of secondary benzyl carbamates - Design of dialkylcarbamates, cleavable under basic, mild conditions

Article abstract of DOI:10.1055/s-1996-4163

Enantiomerically enriched, secondary benzyl N-[2-(tert-butyldiphenylsilyloxy)ethyl]-N-isopropylcarbamates were prepared, lithiated, and stereospecifically substituted by several electrophiles. Deprotection under basic conditions furnished optically active tertiary benzylic alcohols and glycols or 2-hydroxy-2-arylalkanoic acid esters. In summary, the sequence achieves the stereospecific chain elongation of d¹-synthons, derived from secondary benzyl alcohols.