Synthesis of enantioenriched tertiary benzylic alcohols via stereospecific lithiation of secondary benzyl carbamates - Design of dialkylcarbamates, cleavable under basic, mild conditions
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.
Derwing, Christoph,Hoppe, Dieter
p. 149 - 154
(2007/10/03)
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