Stereoselective conversión of keto groups into methyl vinyl quaternary carbón centers

BL Buckwalter, IR Burfitt, H Felkin…

Index: Buckwalter,B.L. et al. Journal of the American Chemical Society, 1978 , vol. 100, p. 6445 - 6450

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Citation Number: 50

Abstract

Abstract: In the presence of bis (tripheny1phosphine) nickel dichloride both trans-(lb) and cis- 4-tert-butyl-1-vinylcyclohexano1 (IC) reacted with methylmagnesium bromide affording r-4- tert-butyl-t-1-methyl-I-vinylcyclohexane (4a), 1-n-propyli-dene-4-tert-butylcyclohexane (3b), and r-4-tert-butyl-c-1-methyl-1-vinylcyclohexane (Sa) in a 19: 5: I ratio. This reaction was applied to vinylcarbinols prepared from four manool-derived 13-hydrophenanthrones (8, ...

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