Trifluoromethanesulfonamide pyrrolidine

S)-Pyrrolidine trifluoromethanesulfonamide 3a is a highly active catalyst for the asymmetric conjugate addition of aldehydes and ketones to nitroalkenes. The use of catalyst 3a (20 mol%) in i-PrOH at 0 °C, afforded a,a-dialkyl aldehydes with good to high yields and high to excellent levels of diastereo- and enantioselectivity (Scheme 9.20). In addition, the reactions of various cyclic and acyclic ketones with aromatic nitro-olefins indicated the usefulness of the catalyst. " Computational results corresponded with the observed stereoselectivities of 3a-catalysed Michael reactions. 

For example, in 2004, Wang and coworkers reported a series of asymmetric transformations, for example, a-aminoxylahon, Mannich reactions, and a-sulfenylation, under the catalysis of pyrrolidine trifluoromethanesulfonamide 36 the product yields and diastereo- and enanhoselectivities are quite good in most... 

Wang and co-workers have developed (5)-pyrrolidine trifluoromethanesulfonamide 41 as a new L-proline-type organocatalyst. The catalytic activity of 41 is sometimes superior to that of L-prohne, and conjugate addition is one such example. A wide range of aldehydes and ketones reacted with nitroolefins in the presence of 41 with high... 

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