Catalytic enantioselective aza-Diels–Alder reactions of unactivated acyclic 1,3-dienes with aryl-, alkenyl-, and alkyl-substituted imines.

Autor: Hatanaka, Yasuo, Nantaku, Shuuto, Nishimura, Yuhki, Otsuka, Tomoyuki, Sekikaw, Tohru
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Zdroj: Chemical Communications; 8/18/2017, Vol. 53 Issue 64, p8996-8999, 4p
Abstrakt: A catalytic enantioselective aza-Diels–Alder reaction of unactivated acyclic dienes with aryl-, alkenyl-, and alkyl-substituted imines is described. With 5–10 mol% loadings of a new Brønsted acid catalyst, the aza-Diels–Alder reaction of unactivated acyclic dienes proceeded to give the corresponding aza-Diels–Alder adducts in high yields (up to 98%) with excellent enantioselectivity (up to 98% ee). Preliminary DFT calculations suggest that the reaction proceeds through a chiral ion pair intermediate. [ABSTRACT FROM AUTHOR]
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