SmI2-promoted intramolecular asymmetric pinacol-type ketone-tert-butanesulfinyl imine reductive coupling: stereoselectivity and mechanism.
The asymmetric ketone-tert-butanesulfinyl (t-BS) imine pinacol-type reductive coupling promoted by SmI(2) is described. Trans-1,2-vicinal amino alcohols were formed predominantly in excellent er and high dr. The stereochemical outcome provided evidence for a radical mechanism for SmI(2)-induced reductive couplings of t-BS imines.
Wang
Bing
B
Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433, China. wangbing@fudan.edu.cn
Wang
Yong-Jun
YJ
D000605:Amino Alcohols / Q000737:chemistry; D018360:Crystallography, X-Ray; D003500:Cyclization; D007097:Imines / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D000605:Amino Alcohols; D007097:Imines; D007659:Ketones