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Highly Enantioselective Epoxidation of 2,4‐Diarylenones by Using Dimeric Cinchona Phase‐Transfer Catalysts: Enhancement of Enantioselectivity by Surfactants

2005; Wiley; Volume: 44; Issue: 9 Linguagem: Inglês

10.1002/anie.200462254

1521-3773

Sang‐sup Jew, Jeong‐Hee Lee, Byeong‐Seon Jeong, Mi‐Sook Yoo, Mi‐Jeong Kim, Yeon‐Ju Lee, Jihye Lee, Sea‐hoon Choi, Kyungjae Lee, Myoung Soo Lah, Hyeung‐geun Park,

Oxidative Organic Chemistry Reactions

Dramatic increases in reaction rates and enantioselectivities can be effected by the use of surfactants for the phase-transfer catalytic epoxidation of aromatic enones. Based on the X-ray crystal structure of the most effective catalyst—a modified cinchona alkaloid—a plausible transition state of the reaction has been modeled (see picture; HOO− yellow, C gray, H white, N blue, O red). Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2005/z462254_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.