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Lewis Acid Controlled Regioselective 1,2 and 1,4 Reaction of α , β ‐Unsaturated Carbonyl Compounds with Ti IV Enolates Derived from α ‐Diazo β ‐Keto Carbonyl Compounds
Author(s) -
Deng Guisheng,
Tian Xue,
Qu Zhaohui,
Wang Jianbo
Publication year - 2002
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 - 10.1002/1521-3773(20020802)41:15<2773::aid-anie2773>3.0.co;2-i
Subject(s) - regioselectivity , diazo , chemistry , lewis acids and bases , medicinal chemistry , carbonyl group , ketone , organic chemistry , catalysis
The selective generation of 1,2‐ and 1,4‐addition products ( 3 and 4 , respectively) in the addition of Ti IV enolates 1 to α , β ‐unsaturated carbonyl compounds 2 can be almost completely controlled by the choice of Lewis acid. The high selectivity for 1,4 addition when the enones are activated by TiCl 4 or SnCl 4 is probably a result of the bridging chlorine atoms.