Camphor-based α-bromo ketones for the asymmetric Darzens reaction

…, MC González-Rego, A Linden, JM García…

Index: Palomo; Oiarbide; Sharma; Gonzalez-Rego; Linden; Garcia; Gonzalez Journal of Organic Chemistry, 2000 , vol. 65, # 26 p. 9007 - 9012

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Citation Number: 35

Abstract

(1 R)-2-endo-Bromoacetyl-1, 7, 7-trimethylbicyclo [2.2. 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 α, β-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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