Synfacts 2008(1): 0091-0091  
DOI: 10.1055/s-2007-991418
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Asymmetric 1,4-Addition Reaction of Diphenyl Phosphite to Nitroalkenes

Contributor(s): Benjamin List, Subhas Chandra Pan
M. Terada*, T. Ikehara, H. Ube
Tohoku University, Sendai, Japan
Further Information

Publication History

Publication Date:
18 December 2007 (online)

Significance

An organocatalytic asymmetric 1,4-addition reaction of nitroalkenes with diphenyl phosphite has been developed. Axially chiral guanidine catalyst 1 was found to be effective for this reaction. tert-Butyl methyl ether was the optimal solvent for this reaction. With 1-5 mol% of catalyst 1 good to high yields (84-98%) and excellent enantioselectivities (er = 90:10 to 98:2) were obtained for different nitroalkenes.