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 language | English |
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Pages (from-to) | 4124-4143 |
Number of pages | 20 |
Journal | European Journal of Organic Chemistry |
Volume | 2016 |
Issue number | 24 |
DOIs | |
Publication status | Published - 2016 Aug 1 |
Keywords
- Amino alcohols
- Asymmetric synthesis
- C–C coupling
- Organocatalysis
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry