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

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.

収録刊行物

• Tetrahedron

  Tetrahedron 69 (47), 10003-10008, 2013-11-25

  Pergamon-elsevier science ltd

キーワード

• Organocatalysis
• Asymmetric synthesis
• Primary amino acid
• Michael addition
• DFT calculation

詳細情報

• CRID: 1050001339014616192
• NII論文ID: 120005496498
• DOI: 10.1016/j.tet.2013.09.066
• HANDLE: 2115/57393
• ISSN: 00404020
• Web Site: https://api.elsevier.com/content/article/PII:S0040402013014889?httpAccept=text/xml
• Web Site: https://api.elsevier.com/content/article/PII:S0040402013014889?httpAccept=text/plain
• 本文言語コード: en
• 資料種別: journal article
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