Synfacts 2011(6): 0681-0681  
DOI: 10.1055/s-0030-1260417
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Catalytic Asymmetric Chlorocyclization of Unsaturated Amides to Heterocycles

Contributor(s): Benjamin List, Anna Lee
A. Jaganathan, A. Garzan, D. C. Whitehead, R. J. Staples, B. Borhan*
Michigan State University, East Lansing, USA
Further Information

Publication History

Publication Date:
19 May 2011 (online)

Significance

A highly efficient catalytic asymmetric chlorocyclization of unsaturated amides was reported. In the presence of a small amount of catalyst (1-2 mol%), the products were obtained in high yields and excellent enantioselectivities. A broad range of substrates was tolerated, including both aliphatic and aromatic residues on the olefin. Moreover, the authors showed the synthetic utility of the reaction by converting the products into amino alcohols without loss of enantio­purity.