articleAngewandte Chemie International EditionApr 20, 2022Closed access

Beyond Bioisosteres: Divergent Synthesis of Azabicyclohexanes and Cyclobutenyl Amines from Bicyclobutanes**

KDKushal DhakeKWKyla WoelkJBJoseph BecicaAUAndy UnSESarah E. Jenny

University of Victoria · Temple University

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Abstract

Abstract The development of two divergent and complementary Lewis acid catalyzed additions of bicyclobutanes to imines is described. Microscale high‐throughput experimentation was integral to the discovery and optimization of both reactions. N ‐arylimines undergo formal (3+2) cycloaddition with bicyclobutanes to yield azabicyclo[2.1.1]hexanes in a single step; in contrast, N ‐alkylimines undergo an addition/elimination sequence to generate cyclobutenyl methanamine products with high diastereoselectivity. These new products contain a variety of synthetic handles for further elaboration, including many functional groups relevant to pharmaceutical synthesis. The divergent reactivity observed is attributed to…

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Topics & keywords

Topics
Keywords
  • Nucleophile
  • Chemistry
  • Reactivity (psychology)
  • Yield (engineering)
  • Carbocation
  • Lewis acids and bases
  • Cycloaddition
  • Combinatorial chemistry
UN Sustainable Development Goals
  • Clean water and sanitation
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