Premium
Intramolecular Aza‐Anti‐Michael Addition of an Amide Anion to Enones: A Regiospecific Approach to Tetramic Acid Derivatives
Author(s) -
Bi Xihe,
Zhang Jingping,
Liu Qun,
Tan Jing,
Li Bing
Publication year - 2007
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.200600542
Subject(s) - chemistry , enone , michael reaction , intramolecular force , regioselectivity , nucleophile , amide , aryl , nucleophilic addition , conjugated system , stereochemistry , organic chemistry , catalysis , alkyl , polymer
A novel intramolecular aza‐anti‐Michael addition was disclosed in the one‐pot reactions between 3‐oxobutanamides and aryl (heteroaryl) aldehydes under basic conditions, in which amide anions regiospecifically attacked the α‐carbon of an enone fragment, providing a new route to biologically important tetramic acid derivatives. An explanation for the unexpected regioselectivity is proposed based on the results of experiments and theoretical calculations, which is ascribed to (1) the conjugated and rigid molecular skeleton, and (2) proximity effects of the nucleophilic site and the enone α‐carbon.