Diastereodivergent Access to Syn and Anti 3,4-Substituted beta-Fluoropyrrolidines: Enhancing or Reversing Substrate Preference

作者：Fjelbye Kasper; Marigo Mauro; Clausen Rasmus Praetorius; Juhl Karsten^*

来源：Organic Letters, 2016, 18(5): 1170-1173.

DOI：10.1021/acs.orglett.6b00293

A practical diastereodivergent access to beta-fluoropyrrolidines with two adjacent stereocenters has been demonstrated, by either enhancing or completely reversing the substrate control, in the diastereoselective fluorination of a series of diverse pyrrolidinyl carbaldehydes using organocatalysis. Furthermore, enamine catalysis has been successfully utilized for kinetic resolution, obtaining a fluorinated beta-prolinol analogue with two adjacent tetrasubstituted chiral centers in 95% ee from a racemic substrate.

• 出版日期2016-3-4