86. Catalytic Asymmetric Synthesis of Syn-Aldol Products from Intermolecular C−H Insertions between Allyl Silyl Ethers and Methyl Aryldiazoacetates

Authors: Huw M. L. Davies , Evan G. Antoulinakis , and Tore Hansen

Org. Lett.,

1999, 1 (3), 383–386

Rh2(R-DOSP)4-catalyzed decomposition of methyl aryldiazoacetate in the presence of allyl silyl ethers results in a regioselective C−H insertion. The resulting β-siloxy esters are formed with high enantioselectivity (74−92% ee) and diastereoselectivity (96−98% de) when trans-disubstituted allyl silyl ethers are used as substrates.

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