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The azetidine moiety is a privileged motif in medicinal chemistry and new methods that access them efficiently are highly sought after. Towards this goal, we have found that azabicyclo[1.1.0]butyl carbinols, readily obtained from the highly strained azabicyclo[1.1.0]butane (ABB), can undergo divergent strain‐release reactions upon N‐activation. Treatment with trifluoroacetic anhydride or triflic anhydride triggered a semipinacol rearrangement to give keto 1,3,3‐substituted azetidines. More than 20 examples were explored, enabling us to evaluate selectivity and the migratory aptitude of different groups. Alternatively, treatment of the same alcohols with benzyl chloroformate in the presence of NaI led to iodohydrin intermediates which gave spiroepoxy azetidines upon treatment with base. The electronic nature of the activating agent dictates which pathway operates.
- ring expansion
- strained molecules
FingerprintDive into the research topics of 'Divergent, Strain‐Release Reactions of Azabicyclo[1.1.0]butyl Carbinols: Semipinacol or Spiroepoxy Azetidine Formation'. Together they form a unique fingerprint.
- 1 Finished
The development of strain-release-driven transformations: 1,2-metallate and semipinacol rearrangement reactionsAuthor: Gregson, C. H. U., 28 Sep 2021
Supervisor: Aggarwal, V. (Supervisor)
Student thesis: Doctoral Thesis › Doctor of Philosophy (PhD)File