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

Yoshida, Masanori; Nagasawa, Yuki; Kubara, Ami et al.

Tetrahedron, 2013, 69(47), 10003-10008

Permalink : https://hdl.handle.net/2115/57393

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アクセス権
open access
URI
https://hdl.handle.net/2115/57393
タイトル
Mechanistic study of asymmetric Michael addition of malonates to enones catalyzed by a primary amino acid lithium salt
著者
Yoshida, Masanori ; Nagasawa, Yuki ; Kubara, Ami ; Hara, Shoji ; Yamanaka, Masahiro
e-Rad_Researcher
30322829
著者名
Yoshida, Masanori
著者名
Nagasawa, Yuki
著者名
Kubara, Ami
著者名
Hara, Shoji
著者名
Yamanaka, Masahiro
言語
英語
キーワード
Organocatalysis
Asymmetric synthesis
Primary amino acid
Michael addition
DFT calculation
発行日
2013-11-25
出版者
Pergamon-elsevier science ltd
収録物名
Tetrahedron
巻(号)
69(47)
ページ
10003-10008
抄録
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.
資源タイプ
学術雑誌論文
出版タイプ
Accepted Manuscript
PISSN
0040-4020
関連情報 (isVersionOf)
出版社版DOI
https://doi.org/10.1016/j.tet.2013.09.066