Abstract
A new asymmetric approach to assemble cis-vinyl aziridines is reported. A reaction of strategically substituted dienolates, decorated with a γ-leaving group, with chiral sulfinimines afforded chiral vinyl aziridine products in good to excellent yields. This is the first systematic study toward the realization of a useful asymmetric vinylogous aza-Darzens reaction. The reaction is initiated by a syn-selective addition, affording cis-vinyl aziridine products after displacement of bromide. The low syn-diastereoselectivity is attributed to competing retro-Mannich pathways.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 4942-4945 |
| Number of pages | 4 |
| Journal | Organic Letters |
| Volume | 20 |
| Issue number | 16 |
| DOIs | |
| State | Published - Aug 17 2018 |
| Externally published | Yes |
ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry
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CCDC 1451253: Experimental Crystal Structure Determination
Chogii, I. (Creator), Das, P. (Creator), Delost, M. D. (Creator), Crawford, M. N. (Creator) & Njardarson, J. T. (Creator), Cambridge Crystallographic Data Centre, 2018
DOI: 10.5517/ccdc.csd.cc1kq4m1, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1kq4m1&sid=DataCite
Dataset
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CCDC 1451353: Experimental Crystal Structure Determination
Chogii, I. (Creator), Das, P. (Creator), Delost, M. D. (Creator), Crawford, M. N. (Creator) & Njardarson, J. T. (Creator), Cambridge Crystallographic Data Centre, 2018
DOI: 10.5517/ccdc.csd.cc1kq7vc, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1kq7vc&sid=DataCite
Dataset