Asymmetric synthesis of cis-5-tert-butylproline with metal carbenoid NH insertion.
The highly stereoselective intramolecular metal carbenoid insertion reaction of sulfinimine-derived delta-amino alpha-diazoesters is used to prepare cis-5-tert-butylproline. A concerted or nearly concerted metal carbenoid N-H insertion reaction mechanism is proposed.
Davis
Franklin A
FA
Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122, USA. fdavis@temple.edu
Yang
Bin
B
Deng
Jianghe
J
D000588:Amines / Q000737:chemistry; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods; D004952:Esters / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D011392:Proline / Q000031:analogs & derivatives* / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
D000588:Amines; D004952:Esters; D007659:Ketones; D009942:Organometallic Compounds; D011392:Proline; D012238:Rhodium