Five-membered ring spiro-annulation via thermal rearrangement of enol silyl ethers of 2-(cyclopropylmethylene) cycloalkanones. A formal total synthesis of some …
E Piers, CK Lau, I Nagakura
Index: Piers, Edward; Lau, Cheuk Kun; Nagakura, Isao Canadian Journal of Chemistry, 1983 , vol. 61, p. 288 - 297
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Citation Number: 18
Abstract
Treatment of the 2-(iodomethylene) cycloalkanones 10 and 11 with lithium (phenylthio)( cyclopropyl) cuprate provided good yields of the corresponding β-cyclopropyl enones 12 and 13, respectively. Thermolysis of the latter substances produced relatively poor yields of the desired spiro-annulation products 14 and 15. However, conversion of 12 and 13 into the corresponding enol silyl ethers 24 and 25, followed by thermal rearrangement of the latter ...
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