Allyl amines carbometallation

ZIRCONIUM-CATALYZED ENANTIOSELECTIVE CYCLIC CARBOMETALLATION OF ALLYLIC ETHERS, ALCOHOLS, AMINES, AND SULFIDES... 

The formation and control of chiral quaternary centers by multicomponent reactions is undoubtedly a challenging task. The combination of a carbometalation reaction of chiral alkynyl sulfoxide 33, followed by a zinc homologation and an allylation in a four-component process, allowed the preparation of homoallylic alcohols or amines 34 bearing tertiary and quaternary stereocenters in a single step with high yields and diastereoselectivities (Scheme 11.13). The zinc carbenoid used in this reaction can be prepared independently or in situ by the reaction of diethyl zinc and diiodomethane. This carbenoid readily homologates the vinyl copper into the allylic species, which reacted diastereoselectively with aldehydes, to give the expected products. The chiral sulfinyl moiety can be easily removed by treatment with alkyllithi-ums, which allows a further functionalization of the carbon skeleton [35]. 

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