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Synthesis 1996; 1996(1): 149-154
DOI: 10.1055/s-1996-4163
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Synthesis of Enantioenriched Tertiary Benzylic Alcohols via Stereospecific Lithiation of Secondary Benzyl Carbamates - Design of Dialkylcarbamates, Cleavable under Basic, Mild Conditions

Christoph Derwing, Dieter Hoppe*
  • *Organisch-chemisches Institut der Universität Münster, Corrensstraße 40, D-48149 Münster, Germany, Fax +49(251)839772
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Publikationsdatum:
31. Dezember 2000 (online)

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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.

lithiated benzyl carbamates - chiral configurationally stable ion pairs - stereospecifity of electrophilic substitution - enantioselective synthesis - tertiary benzylic alcohols - O-protecting groups

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