Scripps VIVO scripps research logo

  • Index
  • Log in
  • Home
  • People
  • Organizations
  • Research
  • Events
Search form

Pipecolic acid-catalyzed direct asymmetric mannich reactions

Academic Article
uri icon
  • Overview
  • Identity
  • Additional Document Info
  • View All
scroll to property group menus

Overview

authors

  • Cheong, P. H. Y.
  • Zhang, H. L.
  • Thayumanavan, R.
  • Tanaka, F.
  • Houk, K. N.
  • Barbas III, Carlos

publication date

  • March 2006

journal

  • Organic Letters  Journal

abstract

  • Mannich reactions between aldehydes and N-p-methoxyphenyl-protected alpha-imino ethyl glyoxylate have been performed using (S)-pipecolic acid as catalyst. The reactions give both syn- and anti-products (dr=1.4-2:1) with high enantioselectivities (>98% ee). In contrast, (S)-proline-catalyzed reactions give mainly syn-products with high enantioselectivities. Computational studies reveal that the energetic preference between the transition structures involving the s-cis-enamine and the s-trans-enamine is smaller for the pipecolic acid as compared to proline, yielding the (2S,3R)-anti and the (2S,3S)-syn Mannich product in nearly equal amounts.

subject areas

  • Aldehydes
  • Catalysis
  • Glyoxylates
  • Molecular Structure
  • Pipecolic Acids
  • Proline
  • Stereoisomerism
  • Thermodynamics
scroll to property group menus

Identity

PubMed Central ID

  • PMC3164113

International Standard Serial Number (ISSN)

  • 1523-7060

Digital Object Identifier (DOI)

  • 10.1021/ol052861o

PubMed ID

  • 16494447
scroll to property group menus

Additional Document Info

start page

  • 811

end page

  • 814

volume

  • 8

issue

  • 5

©2021 The Scripps Research Institute | Terms of Use | Powered by VIVO

  • About
  • Contact Us
  • Support