Switchable Diastereoselectivity in Enantioselective [4+2] Cycloadditions with Simple Olefins by Asymmetric Binary Acid Catalysis | Zendy

Lv Jian | Zendy; Zhang Long | Zendy; Luo Sanzhong | Zendy; Cheng JinPei | Zendy

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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 ).

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