Temperature-Dependent Enantio- and Diastereodivergent Synthesis of Amino Acids with One or Multiple Chiral Centers

Org Lett. 2017 Sep 1;19(17):4660-4663. doi: 10.1021/acs.orglett.7b02296. Epub 2017 Aug 15.

Abstract

A general and facile methodology for temperature-dependent enantiodivergent and diastereodivergent synthesis of amino acids with one or multiple chiral centers was developed. Camphor-based tricyclic iminolactones attack electrophiles from the endo face at low temperature (-78 to -40 °C) and from the exo face at high temperature (-10 to 25 °C).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemical synthesis*
  • Molecular Structure
  • Stereoisomerism
  • Temperature

Substances

  • Amino Acids