Squaramide-Catalyzed Asymmetric Intramolecular Oxa-Michael Reaction of α,β-Unsaturated Carbonyls Containing Benzyl Alcohol: Construction of Chiral 1-Substituted Phthalans
Eun Chae Son, Seung Yeon Kim and Sung-Gon Kim*
*Department of Chemistry, College of Natural Science, Kyonggi University, 154-42 Gwanggyosan-ro, Yeongtong-gu, Suwon 16227, Republic of Korea,
Email: sgkim123
kyonggi.ac.kr
E. C. Son, S. Y. Kim, S.-G. Kim, J. Org. Chem., 2021, 86, 6826-6839.
DOI: 10.1021/acs.joc.1c00715
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Abstract
Using a cinchona squaramide-based organocatalyst, an enantioselective intramolecular oxa-Michael reaction of enones as well as α,β-unsaturated esters containing benzylic alcohols provided their corresponding 1,3-dihydroisobenzofuranyl-1-methylene ketones and 1,3-dihydroisobenzofuranyl-1-methylene esters in excellent yields with high enantioselectivities.
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Key Words
1,3-dihydro-2-benzofurans, organocatalysis
ID: J42-Y2021
