Tetrahedron

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

C Kuroda, H Koshio, A Koito, H Sumiya, A Murase…

Index: Kuroda; Koshio; Koito; Sumiya; Murase; Hirono Tetrahedron, 2000 , vol. 56, # 35 p. 6441 - 6455

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Citation Number: 33

Abstract

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] ...