Nazarov cyclization of 4-cycloalkylidene-5-(trimethylsilyl)pent-1-en-3-one derivatives. Synthesis of spiro[4.5]decane, Spiro[4.4]nonane, and Their derivatives
Spiro[4.5]decane and spiro[4.4]nonane ring systems were synthesized by FeCl3-induced Nazarov cyclization of α-(trimethylsilylmethyl)divinyl ketone derivatives. It was found that the double bond position of the product is controlled by the presence/absence of α'-substituent, while trimethylsilyl group is essential to obtain the products in good yields. Spiro[4.4]nonanes having exo-methylene group underwent rearrangement to bicyclo[4.3.0]nonanes. (C) 2000 Elsevier Science Ltd.
Kuroda,Koshio,Koito,Sumiya,Murase,Hirono
p. 6441 - 6455
(2007/10/03)
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