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Switchable Diastereoselectivity in Enantioselective [4+2] Cycloadditions with Simple Olefins by Asymmetric Binary Acid Catalysis
Author(s) -
Lv Jian,
Zhang Long,
Luo Sanzhong,
Cheng JinPei
Publication year - 2013
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201304561
Subject(s) - enantioselective synthesis , simple (philosophy) , binary number , catalysis , chemistry , combinatorial chemistry , computer science , organic chemistry , world wide web , mathematics , philosophy , arithmetic , epistemology
The exchange of the metal ion from In III to Sc III in a binary acid catalyst leads to a switch in the diastereoselectivity of [4+2] cycloadditions. Simple olefins and β,γ‐unsaturated α‐ketoester were thus transformed to the corresponding exo or endo products, respectively, with excellent diastereoselectivity (up to 99:1 d.r.) and enantioselectivity (up to 99 % ee ).