Tetrahedron Letters

A new approach to the synthesis of 1-oxaspiro [4. n] alkanes and tetrahydrofurans by the 1, 5-CH insertion reaction of magnesium carbenoids

T Satoh, T Yasoshima, H Momochi

文献索引：Satoh, Tsuyoshi; Yasoshima, Tsukasa; Momochi, Hitoshi Tetrahedron Letters, 2012 , vol. 53, # 16 p. 2074 - 2077

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被引用次数: 4

摘要

1-Alkoxy-1-[2-chloro-2-(p-tolylsulfinyl) ethyl] cycloalkanes were prepared from various cyclic ketones in good overall yields. Treatment of these cycloalkanes bearing a sulfinyl group with i-PrMgCl resulted in the formation of 1-oxaspiro [4. n] alkanes in high to quantitative yields via the 1, 5-CH insertion reaction of generated magnesium carbenoid intermediates. When this procedure was commenced with acyclic ketones, multi-substituted tetrahydrofurans ...