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Z-Stereoselective Peterson olefination of ketones
Authors:N. Ya. Grigorieva  O. A. Pinsker  A. V. Buevich  A. M. Moiseenkov
Affiliation:(1) N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913 Moscow, Russian Federation
Abstract:
A highly-stereoselective method (90 % of theZ-isomer) was developed for the Peterson olefination of ketones with nerylacetone (1) as an example. The method is based on the introduction of a PhS group, which is removed after completion of the reaction, at the ketone C(3) atom.DeceasedFor the perliminary communication, see Ref. 10.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 509–516, March, 1995.The authors are grateful to the Russian Foundation for Basic Research (grant No. 94.03.08904) and the International Science Foundation (grant NGO000) for financial support of this work.
Keywords:olefination of ketones  stereoselective synthesis  Peterson reaction  2Z- and 2E-4-phenylthiofarnesoles and 2Z- and 2E-4-phenylthiofarnesoates
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