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Enantioselective Tandem O -Nitroso Aldol/Michael Reaction

2004; American Chemical Society; Volume: 126; Issue: 19 Linguagem: Inglês

10.1021/ja049741g

1943-2984

Yuhei Yamamoto, Norie Momiyama, Hisashi Yamamoto,

Asymmetric Hydrogenation and Catalysis

This communication presents studies that illustrated nitroso Diels−Alder adduct has been obtained in uniformly high enantioselectivity via a tandem nitroso aldol/Michael reaction using an amine catalyst. The regiochemical outcome of this construction is documented to be the opposite to that of the normal nitroso aldol reaction, which has been determined by X-ray analysis. The reaction of the enone with silver−BINAP catalyst has also been investigated in conjunction with the control of regiochemistry in a stepwise process.