Catalytic Efficiency of Primary β‐Amino Alcohols and Their Derivatives in Organocatalysis. Issue 24 (26th April 2016)

• Record Type: Journal Article
• Authors: Reddy, Ummareddy Venkata Subba; Chennapuram, Madhu; Seki, Chigusa; Kwon, Eunsang; Okuyama, Yuko; Nakano, Hiroto
• Is Part Of: European journal of organic chemistry. Issue 24(2016)
• Page Start: 4124
• Page End: 4143
• Publication Date: 2016-04-26
• Subjects: Organocatalysis -- Asymmetric synthesis -- C–C coupling -- Amino alcohols; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201600164
• Languages: English
• ISSNs: 1434-193X

Abstract

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. Abstract : This review demonstrates the catalytic efficiency of primary β‐amino alcohols and their derivatives in organocatalysis. These simple amino alcohols are inexpensive alternatives to other primary amino organocatalysts, being easy to synthesize and air‐stable and offering the potential for introduction of different functional groups and alteration of steric sites.