Premium
Asymmetric Diels–Alder Reactions of 2,4,6‐Trienals via Tetraenamine Catalysis
Author(s) -
Zhou QingQing,
Xiao YouCai,
Yuan Xin,
Chen YingChun
Publication year - 2014
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201400015
Subject(s) - chemistry , regioselectivity , oxindole , stereoselectivity , diene , diels–alder reaction , catalysis , organic chemistry , natural rubber
While significant progress has been made in Diels–Alder cycloadditions of 2,4‐dienals by the formation of trienamine intermediates, we report that the further extended tetraenamine species can be generated from 2,4,6‐trienal substrates, which subsequently act as 3,6‐regioselective diene partners in asymmetric Diels–Alder reaction with 3‐olefinic oxindole dienophiles. An array of highly functionalized spirocyclic compounds were produced in good stereoselectivity up to 96 % ee and greater than 19:1 d.r., and with fair to moderate yields of 40–67 %.