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Primary‐Amine‐Catalyzed Enantioselective Intramolecular Aldolizations
Author(s) -
Zhou Jian,
Wakchaure Vijay,
Kraft Philip,
List Benjamin
Publication year - 2008
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200802497
Subject(s) - cinchona , enantioselective synthesis , ketone , intramolecular force , chemistry , amine gas treating , enantiomer , catalysis , acetic acid , organic chemistry , cyclohexene , aldol reaction , combinatorial chemistry
Aldol cyclodehydration of 4‐substituted‐2,6‐heptanediones leads to enantiomerically enriched 5‐substituted‐3‐methyl‐2‐cyclohexene‐1‐ones, which serve as perfume ingredients and valuable synthetic building blocks. Primary amines derived from cinchona alkaloids in combination with acetic acid are efficient catalysts for this transformation, which deliver both enantiomers of the celery ketone.