Chiral Phosphoric Acid Catalyzed Intramolecular Oxo-Michael
Reactions

doi:10.1055/s-0029-1220115

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Synfacts 2010(7): 0828-0828
DOI: 10.1055/s-0029-1220115

Organo- and Biocatalysis

Chiral Phosphoric Acid Catalyzed Intramolecular Oxo-Michael Reactions

Contributor(s): Benjamin List, Steffen Müller
Q. Gu, Z.-Q. Rong, C. Zheng, S.-L. You*
Shanghai Institute of Organic Chemistry, P. R. of China

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Publikationsdatum:
22. Juni 2010 (online)

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Significance

This work describes the desymmetrization of cyclohexadienones utilizing a chiral phosphoric acid 1 catalyzed intramolecular oxo-Michael addition. In the presence of 1 different cyclohexadienones cyclized readily to give the corresponding products in high yields and enantioselectivities. The versatility of this reaction was demonstrated in the asymmetric synthesis of three cleroindicin natural products.