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2005
Carboxylic acid esters
P 0360
Catalytic Asymmetric Reactions for Organic Synthesis: The Combined
Activation/Siloxy-Cope Rearrangement. — The Rh-catalyzed reaction of
19- 074 C—H
vinyldiazoacetates with allyl silyl ethers results in stereoselective formation of C—H
insertion products like (III), (VII), and (XI). Under thermal or microwave conditions
they easily undergo stereoselective siloxy-Cope rearrangement to afford esters of type
(IV), (V), (VIII), (X), and (XII). The procedure thus represents a novel and practical
approach to γ,δ-substituted α,β-unsaturated carboxylic acid esters. — (DAVIES*, H.
M. L.; BECKWITH, R. E. J.; J. Org. Chem. 69 (2004) 26, 9241-9247; Dep. Chem.,
State Univ. N. Y., Buffalo, NY 14260, USA; Eng.) — Jannicke
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