Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 40, Pages 12229-12233Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201705202
Keywords
azetidine; aziridine; carbene; enantiospecific; rearrangement
Categories
Funding
- NIH [R01 GM11412]
- ACS-PRF [53146-ND1]
- National Science Foundation (NSF) [CHE-9208463, CHE-9629688]
- National Institutes of Health (NIH) [RR08389-01, 1S10OD020022-1]
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The reaction of rhodium-bound carbenes with strained bicyclic methylene aziridines results in a formal [3+1] ring expansion to yield highly substituted methylene azetidines with excellent regio- and stereoselectivity. The reaction appears to proceed through an ylide-type mechanism, where the unique strain and structure of the methylene aziridine promotes a ring-opening/ring-closing cascade that efficiently transfers chirality from substrate to product. The resultant products can be elaborated into new azetidine scaffolds containing vicinal tertiary-quaternary and even quaternary-quaternary stereocenters.
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