Tetrahedron letters

[1, 3] Sigmatropic rearrangement of ketene silyl acetals derived from benzyl α-substituted propanoates

I Shiina, H Nagasue

Index: Shiina, Isamu; Nagasue, Hiroshi Tetrahedron Letters, 2002 , vol. 43, # 33 p. 5837 - 5840

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Citation Number: 13

Abstract

A novel [1, 3] sigmatropic rearrangement of ketene silyl acetals derived from benzyl α- substituted propanoates is developed. The reaction of ketene silyl acetal derived from optically active 1-phenylethyl 2-methylpropanoate mainly proceeds with the retention of chirality at the benzyl position to give the corresponding optically active silyl ester under thermodynamic conditions.