Umpolung Synthesis of 1,3-Amino Alcohols: Stereoselective Addition of 2-Azaallyl Anions to Epoxides.

Journal Article (Journal Article)

We report the direct preparation of 1,3-amino alcohols that contain up to three contiguous stereogenic centers by the umpolung coupling of imines and epoxides. Nucleophilic 2-azaallyl anions, generated from imines, are stereoselectively added to epoxides to furnish 1,3-amino alcohols after hydrolysis of the product imine. Transformations afford amino alcohols with >98% site selectivity with respect to both reaction partners and in up to >98% yield and >20:1 dr.

Full Text

Duke Authors

Cited Authors

  • Daniel, PE; Weber, AE; Malcolmson, SJ

Published Date

  • July 2017

Published In

Volume / Issue

  • 19 / 13

Start / End Page

  • 3490 - 3493

PubMed ID

  • 28656772

Electronic International Standard Serial Number (EISSN)

  • 1523-7052

International Standard Serial Number (ISSN)

  • 1523-7060

Digital Object Identifier (DOI)

  • 10.1021/acs.orglett.7b01471


  • eng