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8307318 
Journal Article 
Enantioselective synthesis of (R)-convolutamydine A with new N-heteroarylsulfonylprolinamides 
Nakamura, S; Hara, N; Nakashima, H; Kubo, K; Shibata, N; Toru, T; , 
2008 
Yes 
Chemistry: A European Journal
ISSN: 0947-6539
EISSN: 1521-3765 
14 
27 
8079-8081 
English 
18666290 
Synthesis of (R)-convolutamydine A and its derivatives by using a catalytic amount of novel N-heteroarylsulfonylprolinamide organocatalyst was reported. The results show that the catalyst loading of N-(2-thienylsulfonyl)prolinamide can be reduced to 2 mol% without loss of enantioselectivity. It is found that recrystallization of 95% ee convolutamydine A from hexane/ethyl acetate results in an enantiomerically pure (R)-convolutamydine. The hydrogen bonding between the amide proton and the 2-thienyl sulfur atom in the chiral organocatalyst plays an important role in the enantioselectivity. The results also show that the reaction using N-(2-thienylsulfonyl)prolinamide proceeds through the anti-trans-transition state (TS) to give (R)-convolutamydine A. 
Aldol reaction; Enantioselectivity heteroarylsulfonyl groups; Hydrogen bonds; Organocatalysis