Synthesis of Enantioenriched Tertiary Benzylic Alcohols via Stereospecific Lithiation of Secondary Benzyl Carbamates - Design of Dialkylcarbamates, Cleavable under Basic, Mild Conditions
- 1 January 1996
- journal article
- research article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 1996 (01) , 149-154
- https://doi.org/10.1055/s-1996-4163
Abstract
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.Keywords
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