Asymmetric synthesis of terminal N-tert-butylsulfinyl aziridines from organoceriums and an alpha-chloroimine.

Authors :: Hodgson DM
Kloesges J
Evans B
Source :: Organic letters [Org Lett] 2008 Jul 03; Vol. 10 (13), pp. 2781-3. Date of Electronic Publication: 2008 Jun 04.
Publication Year :: 2008
Abstract: Addition of N-(2-chloroethylidene)- tert-butylsulfinamide to organocerium reagents in DMPU/THF (1:10) at -78 degrees C followed by warming to 25 degrees C provides terminal N-tert-butylsulfinyl aziridines in good yields (63-92%, nine examples) and diastereomeric ratios (85:15- >99:1).

Subjects :: Aziridines chemistry
Molecular Structure
Oxidation-Reduction
Stereoisomerism
Sulfur Compounds chemistry
Aziridines chemical synthesis
Cerium chemistry
Hydrocarbons, Chlorinated chemistry
Imines chemistry
Organic Chemicals chemistry
Sulfur Compounds chemical synthesis

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