Organic Letters
Organic Letters
5 years ago

Useful Applications of Enantioselective (4 + 2)-Cycloaddition Reactions to the Synthesis of Chiral 1,2-Amino Alcohols, 1,2-Diamines, and β-Amino Acids

Useful Applications of Enantioselective (4 + 2)-Cycloaddition Reactions to the Synthesis of Chiral 1,2-Amino Alcohols, 1,2-Diamines, and β-Amino Acids
Barla Thirupathi, Karla Mahender Reddy, E. J. Corey
The scope of enantioselective (4 + 2)-cycloaddition reactions has been expanded to include reactive olefinic components that are equivalents of three inoperable and unstable ethylene derivatives: 1-hydroxy-2-aminoethylene, 1,2-diaminoethylene, and β-aminoacrylic acid. In this way, a variety of otherwise unavailable functionalized (4 + 2)-cycloadducts have been synthesized from 1,3-dienes with high enantioselectivity (92–98%) and in good yields. The research leading up to this synthetic advance has also produced some surprising insights on reactivity and positional selectivity in catalytic enantioselective (4 + 2)-cycloaddition.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02437

DOI: 10.1021/acs.orglett.7b02437

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