Journal of the American Chemical Society 2002-03-13

A new two-step four-component synthesis of highly functionalized cyclohexenols by sequential nickel-catalyzed couplings.

Mario Lozanov, John Montgomery

Index: J. Am. Chem. Soc. 124 , 2106-2107, (2002)

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Abstract

A new two-step procedure for the synthesis of cyclohexenols has been developed. A nickel-catalyzed three-component addition of an enal, alkyne, and acetylenic tin affords substituted hept-4-en-6-ynals. The products of this first step then undergo a second nickel-catalyzed reaction with organozincs or organoboranes to afford densely functionalized cyclohexenols. Variation in each of the four components is tolerated to provide access to a wide range of versatile building blocks.