Regioselective addition of 1-trimethylsilyloxy-1-methoxy-1, 3-dienes to aldonitrones catalysed by trimethylsilyl triflate

C Camiletti, DD Dhavale, F Donati, C Trombini

Index: Camiletti, Chiara; Dhavale, Dilip D.; Donati, Franco; Trombini, Claudio Tetrahedron Letters, 1995 , vol. 36, # 40 p. 7293 - 7296

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Citation Number: 32

Abstract

1-Trimethylsilyloxy-1-methoxy-1, 3-dienes (3a-d) regioselectively add to aldonitrones at− 20° C in dichloromethane in the presence of 10–20% of trimethylsilyl triflate to give γ- adducts in high yields; on the other hand, 1-trimethylsilyloxy-1-methoxy-1, 3-hexadiene (3e) displayes a reversed regiochemical preference affording the α-adduct as the major product.