Tertiary alcohols via carbene insertion reaction

ORGN 112

Chun Sing Li, chunsing_li@merck.com and Guillaume Tessier. Department of Medicinal Chemistry, Merck Frosst Centre for therapeutic Research, P.O. Box 1005, Pointe-Clarie-Dorval, QC H9R 4P8, Canada
Chiral tertiary alcohols are present in numerous natural products and pharmaceutical interested substances. Although many successes were obtained with the enantioselective synthesis of secondary alcohols, preparation of tertiary alcohols in high enantioselectivity is still a continued challenge. Recently, Masaki reported the synthesis of chiral tertiary dichloromethylcarbinols by a stereospecific C-H insertion of dichlorocarbene with protected secondary alcohols (Chem. Lett., 2000, 1180). The potential of this approach is worthwhile in a more detailed study. Herein, we discuss our results with a broader range of substrates and the effects of different parameters such as nature of phase transfer catalysts, temperature, and steric as well as electronic effects on the carbene insertion reaction.

New Reactions and Methodology, Materials, Total Synthesis, Process R&D
8:00 PM-10:00 PM, Sunday, 28 August 2005 Washington DC Convention Center -- Hall A, Poster

8:00 PM-10:00 PM, Monday, 29 August 2005 Washington DC Convention Center -- Hall A, Sci-Mix

Division of Organic Chemistry

The 230th ACS National Meeting, in Washington, DC, Aug 28-Sept 1, 2005