Formal (4+1) Cyclization of Ammonium Ylides with Vinylogous para-Quinone Methides

Abstract

The formal (4+1) cyclization between in situ generated achiral carbonyl-stabilized ammonium ylides and vinylogous p-quinone methides can be carried out under operationally simple conditions, leading to two different double bond regioisomers depending on the conditions used. Apart from these racemic approaches, a first proof-of-concept for enantioselective versions of these reactions was also obtained.

Key words

ammonium ylides - quinone methides - cyclization - regioisomers - stereoselectivity

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