Vinylogous Mukaiyama-Michael reaction

SCHEME 49 Carbon acid-induced vinylogous Mukaiyama-Michael reaction. 

SCHEME 53 Substrate-controUed diastereoselective vinylogous Mukaiyama aldol and vinylogous Mukaiyama-Michael reactions. 

SCHEME 5 7 Enantio- and diastereoselective vinylogous Mukaiyama-Michael reaction catalyzed by chiral binaphthyldiirnide-Ni(n)... 

Q. Zhang, X. Xiao, L. Lin, X. liu, X. Feng, Highly enantioselective synthesis of y-substituted butenolides via the vinylogous Mukaiyama-Michael reaction catalyzed by a chiral scandium(III)-N,N -dioxide complex, Org. Biomol. Chem. 9 (2011) 5748-5754. 

Vinylogous Mukaiyama-Michael additions of 2-trimethylsilyloxyfuran to 3-alkenoyl-2-oxazolidinones to provide 7-butenolides were shown to be /7-selective. The reaction could be rendered enantioselective in the presence of a (T symmetric copper-bisoxazoline complex <1997T17015, 1997SL568> or a l,T-binaphthyl-2,2 -diamine-nickel(ii) complex as catalyst, as depicted in Equation (16) <2004CC1414>. 

The enantioselective vinylogous Mukaiyama—Michael addition of 2-silyloxyfurans to cyclic unsaturated oxo esters afforded a variety of compounds bearing a y-butenolide or y-lactone connected to a cycloalkane or cycloalkene moiety (13JOC2289). The reaction of siloxyfurans with aromatic aldimines could be catalyzed efficiently by silver(I) complexes of the Ar-BlNMOL-derived chiral monophosphine (13T8777). 

Intermolecular Michael addition [4.1] Intermolecular aldol reaction [6.2.1] Intramolecular aldol reaction [6.2.2] Aldol-related reactions (e.g. vinylogous Mukaiyama-type aldol) [6.2.3]... 

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