Synfacts 2010(7): 0828-0828  
DOI: 10.1055/s-0029-1220115
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

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
Further Information

Publication History

Publication Date:
22 June 2010 (online)

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.