Premium
Cross‐conjugated Trienamine Catalysis with α′‐Alkylidene 2‐Cyclohexenones: Application in β,γ‐Regioselective Aza‐Diels–Alder Reaction
Author(s) -
Zhou Zhi,
Wang ZhouXiang,
Ouyang Qin,
Xiao Wei,
Du Wei,
Chen YingChun
Publication year - 2017
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.201605606
Subject(s) - regioselectivity , conjugated system , amine gas treating , catalysis , chemistry , diels–alder reaction , organic chemistry , polymer
Endo ‐type cross‐conjugated trienamines between highly congested α′‐alkylidene 2‐cyclohexenones and a chiral primary amine catalyst serve as HOMO‐raised dienophiles in inverse‐electron‐demand aza‐Diels–Alder cycloadditions with a number of 1‐azadiene substrates. The reactions exhibit exclusive β,γ‐regioselectivity, and multifunctional products with high molecular complexity are efficiently constructed in excellent diastereo‐ and enantioselectivity (>19:1 d.r., up to 99 % ee ).