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| Content Provider | World Health Organization (WHO)-Global Index Medicus |
|---|---|
| Author | Desai, Aman A. Dai, Yijing Patwardhan, Aniruddha P. Zhang, Yu Guan, Yong Lu, Zhenjie Vetticatt, Mathew J. Wulff, William D. López-alberca, Maria P. |
| Description | Author Affiliation: Guan Y ( Department of Chemistry, Michigan State University, East Lansing, MI 48824 (USA), Fax: (001) 517-3353-1793 http://www2.chemistry.msu.edu/faculty/wulff/myweb26/index.htm.) |
| Abstract | Alkynyl aziridines can be obtained from the catalytic asymmetric aziridination (AZ reaction) of alkynyl imines with diazo compounds in high yields and high asymmetric inductions mediated by a chiral boroxinate or BOROX catalyst. In contrast to the AZ reaction with aryl- and alkyl-substituted imines, alkynyl imines react to give cis-substituted aziridines with both diazo esters and diazo acetamides. Remarkably, however, the two diazo compounds give different enantiomers of the cis-aziridine from the same enantiomer of the catalyst. Theoretical considerations of the possible transition states for the enantiogenic step reveal that the switch in enantiomers results from a switch from Si-face to Re-face addition to the imine, which in turn is related to a switch from reaction with an E-imine in the former and a Z-isomer of the imine in the latter. |
| ISSN | 09476539 |
| e-ISSN | 15213765 |
| Journal | Chemistry - A European Journal |
| Issue Number | 43 |
| Volume Number | 20 |
| Language | English |
| Publisher | Wiley-VCH;ChemPubSoc Europe |
| Publisher Date | 2014-10-20 |
| Publisher Place | Germany |
| Access Restriction | Open |
| Subject Keyword | Alkynes Chemical Synthesis Aziridines Chemistry Azo Compounds Catalysis Imines Models, Molecular Stereoisomerism Research Support, N.I.H., Extramural |
| Content Type | Text |
| Resource Type | Article |
| Subject | Organic Chemistry Catalysis |
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