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Asymmetric Remote Addition Reactions of Heterocycle‐Based Dearomative Dienamine or Trienamine Species to 1‐Azadienes: Application to Construct Chiral Azocanes and Azecanes
Author(s) -
Hu Di,
Gao Yang,
Song Xue,
Du Wei,
Chen YingChun
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201901848
Subject(s) - chemistry , regioselectivity , stereoselectivity , amine gas treating , michael reaction , organocatalysis , combinatorial chemistry , stereochemistry , catalysis , enantioselective synthesis , organic chemistry
The dearomative dienamines between a few five‐membered heteroaryl aldehydes and chiral secondary amine catalysts underwent highly regio‐, chemo‐ and stereoselective Michael additions to 1‐azadienes derived from 2‐methylenebenzofuran‐3(2 H )‐ones or 2‐methylenebenzo[ b ]thiophen‐3(2 H )‐ones. The very remote ε‐regioselective Michael‐type additions could be similarly realized by employing the analogous dearomative trienamine species from β‐indolyl unsaturated aldehydes. The resulting multifunctional products enabled the efficient construction of enantioenriched chiral azocane or even azecane frameworks with high molecular complexity.