Synthesis of Enantioenriched Tertiary Benzylic Alcohols via Stereospecific Lithiation of Secondary Benzyl Carbamates - Design of Dialkylcarbamates, Cleavable under Basic, Mild Conditions

All articles of this category 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 d 1 -synthons, derived from secondary benzyl alcohols. lithiated benzyl carbamates - chiral configurationally stable ion pairs - stereospecifity of electrophilic substitution - enantioselective synthesis - tertiary benzylic alcohols - O -protecting groups