Enantioselective synthesis of cyclic sulfamidates by using chiral rhodium-catalyzed asymmetric transfer hydrogenation.
Asymmetric transfer hydrogenation (ATH) of cyclic sulfamidate imines 4 and 9, using a HCO(2)H/Et(3)N mixture as the hydrogen source and well-defined chiral Rh catalysts (S,S)- or (R,R)-2, Cp*RhCl(TsDPEN), effectively produces the corresponding cyclic sulfamidates with excellent yields and enantioselectivities at room temperature within 0.5 h. ATH of 4,5-disubstituted imines 9, having preexisting stereogenic centers, is shown to take place with dynamic kinetic resolution.
Kang
Soyeong
S
Drug Discovery Division, Korea Research Institute of Chemical Technology, P.O. Box 107, Yuseong, Daejeon 305-600, Korea.
Han
Juae
J
Lee
Eun Sil
ES
Choi
Eun Bok
EB
Lee
Hyeon-Kyu
HK
D000577:Amides / Q000138:chemical synthesis*; D002384:Catalysis; D006573:Heterocyclic Compounds, 1-Ring / Q000138:chemical synthesis*; D006865:Hydrogenation; D015394:Molecular Structure; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism; D013440:Sulfides / Q000737:chemistry*
D000577:Amides; D006573:Heterocyclic Compounds, 1-Ring; D013440:Sulfides; D012238:Rhodium