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Steric tuning of C2-symmetric chiral N-heterocyclic carbene in gold-catalyzed asymmetric cyclization of 1,6-enynes
Authors:Ken-ichi Yamada  Yasumasa Matsumoto  Khalid B. Selim  Yasutomo Yamamoto  Kiyoshi Tomioka
Affiliation:1. Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan;2. Department of Pharmaceutical Organic Chemistry, Faculty of Pharmacy, Mansoura University, Mansoura 35516, Egypt;3. Faculty of Pharmaceutical Sciences, Doshisha Women''s College of Liberal Arts, Kodo, Kyotanabe 610-0395, Japan
Abstract:Steric tuning of C2-symmetric chiral N-heterocyclic carbene (NHC) was performed in Au(I)-catalyzed asymmetric cyclization of 1,6-enyne. Higher enantioselectivity was realized when chiral NHC–AuCl/AgSbF6 catalysts whose N-substituent on the NHC overlays the Au–Cl bond was utilized.
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