A new approach to 3-hydroxyprolinol derivatives by samarium diiodide-mediated reductive coupling of chiral nitrone with carbonyl compounds.
A flexible diastereoselective approach to trans-(3S)-hydroxyprolinol derivatives is described, which is based on the samarium diiodide-mediated reductive coupling of the chiral 1-pyrroline N-oxide (nitrone)(S)-10 with carbonyl compounds. The reductive hydroxyalkylation of nitrone 10 with ketones and aromatic aldehydes is highly diastereoselective in establishing the C-2 chiral center of the pyrrolidine ring.
Wu
Shao-Feng
SF
Department of Chemistry and Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, PR China.
Zheng
Xiao
X
Ruan
Yuan-Ping
YP
Huang
Pei-Qiang
PQ
D006801:Humans; D007454:Iodides / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D009589:Nitrogen Oxides / Q000737:chemistry*; D010084:Oxidation-Reduction; D011759:Pyrrolidines / Q000138:chemical synthesis / Q000737:chemistry*; D012493:Samarium / Q000737:chemistry*; D013237:Stereoisomerism
D007454:Iodides; D007659:Ketones; D009589:Nitrogen Oxides; D011759:Pyrrolidines; C015388:nitrones; D012493:Samarium; C409809:samarium diiodide