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Fused N‐Heterocycles with Contiguous Stereogenic Centers Accessed by an Asymmetric Catalytic Cascade Reaction of Tertiary Enamides
Author(s) -
Zhen Li,
Tong Shuo,
Zhu Jieping,
Wang MeiXiang
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201904596
Subject(s) - stereocenter , diastereomer , enamine , enantioselective synthesis , chemistry , ketone , cascade reaction , aryl , stereochemistry , catalysis , cyclopentanone , organocatalysis , ring (chemistry) , combinatorial chemistry , organic chemistry , alkyl
We report in this article a cascade reaction strategy for the synthesis of complex N‐heterocyclic compounds with contiguous and tetrasubstituted stereogenic carbons. Under the sequential catalysis of a chiral binol–Ti complex and BF 3 , cyclopentanone‐derived tertiary enamides undergo an enantioselective enamine addition to ketone carbonyls followed by diastereoselective trapping of the resulting acyliminiums by electron‐rich aryl moieties to furnish four‐ and five‐membered ring‐fused N‐heterocyclic products as the sole diastereomers in high yields with up to 99 % ee .