Diastereomerically and enantiomerically pure 2,3-disubstituted pyrrolidines from 2,3-aziridin-1-ols using a sulfoxonium ylide: a one-carbon homologative relay ring expansion.
An ylide-based aza-Payne rearrangement of 2,3-aziridin-1-ols leads to an efficient process for the preparation of pyrrolidines. The aza-Payne rearrangement under basic reaction conditions favors the formation of epoxy amines. Subsequent nucleophilic attack of the epoxide by the ylide yields a bis-anion, which upon a 5-exo-tet ring-closure yields the desired pyrrolidine, thus completing the relay of the three-membered to the five-membered nitrogen-containing ring system. This process takes place with complete transfer of stereochemical fidelity and can be applied to sterically hindered aziridinols.
Schomaker
Jennifer M
JM
Department of Chemistry, Michigan State University, East Lansing, Michigan 48824, USA.
Bhattacharjee
Somnath
S
Yan
Jun
J
Borhan
Babak
B
D001388:Aziridines / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003622:Dapsone / Q000031:analogs & derivatives / Q000737:chemistry; D015394:Molecular Structure; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D001388:Aziridines; D011759:Pyrrolidines; C036115:sulfoxone; D003622:Dapsone