Journal of the Chemical Society. Perkin transactions I p. 931 - 938 (1996)
Update date:2022-08-03
Topics:
Al-Badri, Hashim
About-Jaudet, Elie
Collignon, Noel
Lithiated α-trimethylsilyl cinnamyl-, prenyl- and crotyl-phosphonate carbanions 4 were generated quantitatively in situ from corresponding phosphonates 1, and their reactions with aldehydes were studied. When reacted at 0 °C with aromatic or aliphatic aldehydes, the cinnamyl derivative 4a gave phosphonodienes 7 in high yield and with high stereoselectivity. In contrast, the prenyl derivative 4b showed strict γ-regioselectivity in its reactions with aromatic aldehydes, leading to cyclic organophosphorus compounds 11; with aliphatic aldehydes, a mixture of corresponding heterocyclic compound 11 as major product, and of phosphonodiene 9, as minor product, was obtained. Reactions of crotyl derivative 4c with aromatic or aliphatic aldehydes were highly γ-regioselective too, and phosphonoalcohols 13 could be isolated upon hydrolysis at -70°C. When warmed near 50°C, alkoxides 12 underwent cyclization reaction to give heterocyclic compounds 14.
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