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Dienamine Activation in the Organocatalytic Asymmetric Synthesis of cis ‐3,4‐Difunctionalized Chromans and Dihydrocoumarins
Author(s) -
Enders Dieter,
Yang Xuena,
Wang Chuan,
Raabe Gerhard,
Runsik Jan
Publication year - 2011
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201100320
Subject(s) - chemistry , organocatalysis , phenols , trimethylsilyl , stereochemistry , reactivity (psychology) , enantioselective synthesis , organic chemistry , catalysis , medicine , alternative medicine , pathology
Dienamine activation wins against oxa‐1,4/1,4 : By using nitrovinyl phenols and enals, aminocatalysis allows the asymmetric synthesis of chromans and dihydrocoumarins bearing a CC double bond at the 3‐position (see scheme; TMS=trimethylsilyl). The new protocol takes advantage of the dienamine reactivity of the enal and avoids the known oxa‐Michael/Michael sequence.