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- Title
A Deprotonation Approach to the Unprecedented Amino‐Trimethylenemethane Chemistry: Regio‐, Diastereo‐, and Enantioselective Synthesis of Complex Amino Cycles.
- Authors
Trost, Barry M.; Wang, Youliang
- Abstract
Abstract: The first realization of the amino‐trimethylenemethane chemistry is reported using a deprotonation strategy to simplify the synthesis of the amino‐trimethylenemethane donor in two steps from commercial and inexpensive materials. A broad scope of cycloaddition acceptors (seven different classes) participated in the chemistry, chemo‐, regio‐, diastereo‐, and enantioselectively generating various types of highly valuable complex amino cycles. Multiple derivatization reactions that further elaborated the initial amino cycles were performed without isolation of the crude product. Ultimately, we applied the amino‐trimethylenemethane chemistry to synthesize a potential pharmaceutical in 8 linear steps and 7.5 % overall yield, which previously was achieved in 18 linear steps and 0.6 % overall yield.
- Subjects
PROTON transfer reactions; TRIMETHYLENEMETHANE; RING formation (Chemistry); CHEMICAL yield; DERIVATIZATION
- Publication
Angewandte Chemie, 2018, Vol 130, Issue 34, p11191
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201805876