Camphor-based alpha-bromo ketones for the asymmetric darzens reaction |
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| Authors: | Palomo Oiarbide Sharma Gonzalez-Rego Linden Garcia Gonzalez |
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| Institution: | Departamento de Quimica Organica, Facultad de Quimica, Universidad del Pais Vasco, Apdo 1072, 20080 San Sebastian, Spain, Organisch-chemisches Institut der Universitat Zurich, Winterthurerstrasse 190, CH-8057 Zurich, Swit. |
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| Abstract: | (1R)-2-endo-Bromoacetyl-1,7,7-trimethylbicyclo2.2.1]heptan-2-ol (endo-2-bromoacetylisoborneol) 4 and its trimethylsilyl ether 3 are presented as efficient reagents for the asymmetric Darzens reaction. From the alpha,beta-epoxy ketone adducts the chiral inductor camphor is removed, by treatment with ceric(IV) ammonium nitrate, to yield the corresponding epoxy acids which are isolated as their dicyclohexylammonium salts. |
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