Mechanistic study of asymmetric Michael addition of malonates to enones catalyzed by a primary amino acid lithium salt

Yoshida, Masanori; Nagasawa, Yuki; Kubara, Ami; Hara, Shoji; Yamanaka, Masahiro

doi:10.1016/j.tet.2013.09.066


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Mechanistic study of asymmetric Michael addition of malonates to enones catalyzed by a primary amino acid lithium salt

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Title:	Mechanistic study of asymmetric Michael addition of malonates to enones catalyzed by a primary amino acid lithium salt
Authors:	Yoshida, Masanori Browse this author →KAKEN DB
	Nagasawa, Yuki Browse this author
	Kubara, Ami Browse this author
	Hara, Shoji Browse this author
	Yamanaka, Masahiro Browse this author
Keywords:	Organocatalysis
	Asymmetric synthesis
	Primary amino acid
	Michael addition
	DFT calculation
Issue Date:	25-Nov-2013
Publisher:	Pergamon-elsevier science ltd
Journal Title:	Tetrahedron
Volume:	69
Issue:	47
Start Page:	10003
End Page:	10008
Publisher DOI:	10.1016/j.tet.2013.09.066
Abstract:	A mechanistic study was carried out for the asymmetric Michael addition reaction of malonates to enones catalyzed by a primary amino acid lithium salt to elucidate the origin of the asymmetric induction. A primary beta-amino acid salt catalyst, O-TBDPS beta-homoserine lithium salt, exhibited much higher enantioselectivity than that achieved with the corresponding catalysts derived from alpha- and gamma-amino acids for this reaction. Detailed studies of the transition states with DFT calculations revealed that the lithium cation and carboxylate group of the beta-amino acid salt catalyst have important roles in achieving high enantioselectivity in the Michael addition reaction of malonates to enones. (C) 2013 Elsevier Ltd. All rights reserved.
Type:	article (author version)
URI:	http://hdl.handle.net/2115/57393
Appears in Collections:	工学院・工学研究院 (Graduate School of Engineering / Faculty of Engineering) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 吉田雅紀

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