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Rhodium‐Catalyzed Annulations of 1,3‐Dienes and Salicylaldehydes/2‐Hydroxybenzyl Alcohols Promoted by 2‐Ethylacrolein
Author(s) -
Li HongShuang,
Xiong Yang,
Zhang Guozhu
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201800796
Subject(s) - chemistry , rhodium , annulation , regioselectivity , hydroacylation , catalysis , denticity , organic chemistry , medicinal chemistry , stereochemistry , crystal structure
A rhodium‐catalyzed 2‐ethylacrolein‐promoted protocol enables the annulation reactions of 1,3‐dienes with either salicylaldehydes or 2‐hydroxybenzyl alcohols leading to 2‐alkylchroman‐4‐ones with high regioselectivity. This research highlights the use of 2‐ethylacrolein which probably serves as a tool of bidentate coordination to rhodium intermediates. Mechanistic studies reveal that the transformation proceeds through the 1,4‐hydroacylation pathway to access unsaturated linear ketones with subsequent oxo‐Michael addition.