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Kinetic Resolution in Chiral Phosphoric Acid Catalyzed Aldol Reactions: Enantioselective Robinson‐Type Annulation Reactions
Author(s) -
Yamanaka Masahiro,
Hoshino Masaya,
Katoh Takuya,
Mori Keiji,
Akiyama Takahiko
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201200338
Subject(s) - enantioselective synthesis , kinetic resolution , chemistry , aldol reaction , phosphoric acid , intramolecular force , cyclohexenone , catalysis , annulation , organocatalysis , organic chemistry , medicinal chemistry
A remarkable kinetic resolution was achieved in a chiral phosphoric acid catalyzed intramolecular aldol reaction. Its combination with an enantioselective Michael reaction resulted in the formation of cyclohexenone derivatives with excellent enantioselectivities. DFT calculations on the intramolecular aldol reaction revealed the importance of the 3,3′‐substituents of the phosphoric acid for the high enantioselectivity in the kinetic resolution process.