Enantio- and Diastereoselective Catalytic Alkylation Reactions with Aziridines
- 11 July 2008
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 130 (31), 10076-10077
- https://doi.org/10.1021/ja8036965
Abstract
The first asymmetric phase transfer catalyzed alkylation reaction of a range of carbon acids with N-sulfonyl aziridines is reported. When 10 mol % of a cinchona derived quaternary ammonium salt was employed as the catalyst under mildly basic conditions, N-o-(trifluoromethane)benzenesulfonyl aziridine was efficiently ring-opened to afford the amino ethylene products in consistently high yields and high enantioselectivities (up to 97% ee). By employing substituted aziridines in single enantiomeric form, the corresponding enantiopure alkylation products could be obtained with a range of pronucleophiles in high yields and moderate to high diastereoselectivities (up to 30:1 dr).Keywords
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