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

Camiletti, Chiara ; Dhavale, Dilip D. ; Donati, Franco ; Trombini, Claudio (1995) Regioselective addition of 1-trimethylsilyloxy-1-methoxy-1,3-dienes to aldonitrones catalysed by trimethylsilyl triflate Tetrahedron Letters, 36 (40). pp. 7293-7296. ISSN 0040-4039

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Official URL: http://linkinghub.elsevier.com/retrieve/pii/004040...

Related URL: http://dx.doi.org/10.1016/0040-4039(95)01468-W

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.

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