Synthetic Access to All Four Stereoisomers of Oxetin

J Org Chem. 2016 Oct 21;81(20):9983-9991. doi: 10.1021/acs.joc.6b01795. Epub 2016 Oct 3.

Abstract

A short synthesis of all four stereoisomers of 3-amino-2-oxetanecarboxylic acid (oxetin) is described. The oxetane core is built using a Paternò-Büchi photochemical [2 + 2] cycloaddition; from the key intermediates, complementary resolution protocols provide access to enantiomerically pure oxetin and epi-oxetin on gram-scale.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Crystallography, X-Ray
  • Cycloaddition Reaction
  • Ethers, Cyclic / chemical synthesis
  • Ethers, Cyclic / chemistry
  • Spectrum Analysis / methods
  • Stereoisomerism

Substances

  • Ethers, Cyclic
  • oxetin