β-Isocupreidine–hexafluoroisopropyl acrylate method for asymmetric Baylis–Hillman reactions

Key features of the β-isocupreidine (β-ICD)-catalyzed asymmetric Baylis–Hillman reaction of aldehydes with 1,1,1,3,3,3-hexafluoroisopropyl acrylate (HFIPA) are presented. In addition, an improved method using azeotropically dried β-ICD is described. Graphical Abstract

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Bibliographic Details
Published inTetrahedron Vol. 62; no. 2; pp. 381 - 389
Main Authors Nakano, Ayako, Kawahara, Sakie, Akamatsu, Saori, Morokuma, Kenji, Nakatani, Mari, Iwabuchi, Yoshiharu, Takahashi, Keisuke, Ishihara, Jun, Hatakeyama, Susumi
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 09.01.2006
Elsevier
Subjects
1,1,1,3,3,3-Hexafluoroisopropyl acrylate
Chemistry
Chemistry, Organic
Organic catalysis
Physical Sciences
Science & Technology
β-Isocupreidine
1,1,1,3,3,3-Hexafluoroisopropyl acrylate
β-Isocupreidine
Organic catalysis
ROUTE
organic catalysis
1,1,1,3,3,3-hexafluoroisopropyl acrylate
IMINES
ESTERS
QUINIDINE
beta-isocupreidine
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Summary:Key features of the β-isocupreidine (β-ICD)-catalyzed asymmetric Baylis–Hillman reaction of aldehydes with 1,1,1,3,3,3-hexafluoroisopropyl acrylate (HFIPA) are presented. In addition, an improved method using azeotropically dried β-ICD is described. Graphical Abstract
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2005.09.072