Catalytic Efficiency of Primary β-Amino Alcohols and Their Derivatives in Organocatalysis

Ummareddy Venkata Subba Reddy, Madhu Chennapuram, Chigusa Seki, Eunsang Kwon, Yuko Okuyama, Hiroto Nakano

Research output: Contribution to journalReview article

18 Citations (Scopus)

Abstract

Chiral primary β-amino alcohols, constuting adjacently positioned Brønsted base and Brønsted acid sites, are emerging as very valuable bifunctional organocatalysts in a wide array of asymmetric organic transformations. Primary β-amino alcohols represent inexpensive alternatives to other primary amino organocatalysts such as chiral diamines and cinchona-alkaloid-derived primary amines, being easy to synthesize and air-stable and offering the potential for introduction of different functional groups and also for alteration of steric sites. Here we reveal the catalytic use of simple primary β-amino alcohols and their derivatives as organocatalysts in Diels–Alder cycloaddition, aldol condensation, Michael addition, 1,3-dipolar cycloaddition, the Morita–Baylis–Hillman reaction, cascade cyclization, allylation of isatins, Friedel–Crafts alkylation and epoxidation of olefins.

Original languageEnglish
Pages (from-to)4124-4143
Number of pages20
JournalEuropean Journal of Organic Chemistry
Volume2016
Issue number24
DOIs
Publication statusPublished - 2016 Aug 1

Keywords

  • Amino alcohols
  • Asymmetric synthesis
  • C–C coupling
  • Organocatalysis

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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