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Enantioselective Tandem O-nitroso Aldol/Michael Reaction

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Journal J Am Chem Soc
Specialty Chemistry
Date 2004 May 13
PMID 15137750
Citations 15
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Abstract

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.

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