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Catalytic activation through metal enolization of nucleophile precursors and synthetic applications to enantioselective Michael additions
Author(s) -
Kanemasa Shuji,
Hasegawa Masayuki,
Ono Fumiyasu
Publication year - 2007
Publication title -
the chemical record
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.61
H-Index - 78
eISSN - 1528-0691
pISSN - 1527-8999
DOI - 10.1002/tcr.20105
Subject(s) - nucleophile , chemistry , electrophile , catalysis , enantioselective synthesis , keto–enol tautomerism , enol , cationic polymerization , lewis acids and bases , michael reaction , organic chemistry , combinatorial chemistry , medicinal chemistry
Catalytic activation methods of nucleophile precursors recently developed in our research group were reviewed in this paper. These include (i) the catalytic double activation method of nucleophile precursors through enol formation and of electrophiles through coordination in alcohols; (ii) the double catalytic activation method by use of both catalytic amounts of chiral Lewis acid and external achiral amine; (iii) the catalytic activation method of nucleophile precursors with a chiral cationic Lewis acid in the presence of molecular sieves; and (iv) the single catalytic activation of nucleophile precursors through metal enolization in alcohol media. © 2007 The Japan Chemical Journal Forum and Wiley Periodicals, Inc. Chem Rec 7: 137–149; 2007: Published online in Wiley InterScience ( www.interscience.wiley.com ) DOI 10.1002/tcr.20105