β-isocupreidine-catalyzed asymmetric Baylis-Hillman reaction of imines

Sakie Kawahara; Ayako Nakano; Tomoyuki Esumi; Yoshiharu Iwabuchi; Susumi Hatakeyama

doi:10.1021/ol035102j

β-isocupreidine-catalyzed asymmetric Baylis-Hillman reaction of imines

Sakie Kawahara, Ayako Nakano, Tomoyuki Esumi, Yoshiharu Iwabuchi, Susumi Hatakeyama

Research output: Contribution to journal › Article › peer-review

187 Citations (Scopus)

Abstract

(Matrix presented) β-Isocupreidine (β-ICD)-catalyzed asymmetric Baylis-Hillman reactions of aromatic imines with 1,1,1,3,3, 3-hexafluoroisopropyl acrylate (HFIPA) give (S)-enriched N-protected-α -methylene-β-amino acid esters. In contrast to the corresponding aldehydes, imines show the opposite enantioselectivity. A mechanistic proposal governed by hydrogen bonding is presented.

Original language	English
Pages (from-to)	3103-3105
Number of pages	3
Journal	Organic letters
Volume	5
Issue number	17
DOIs	https://doi.org/10.1021/ol035102j
Publication status	Published - 2003 Aug 21
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "β-isocupreidine-catalyzed asymmetric Baylis-Hillman reaction of imines",

abstract = "(Matrix presented) β-Isocupreidine (β-ICD)-catalyzed asymmetric Baylis-Hillman reactions of aromatic imines with 1,1,1,3,3, 3-hexafluoroisopropyl acrylate (HFIPA) give (S)-enriched N-protected-α -methylene-β-amino acid esters. In contrast to the corresponding aldehydes, imines show the opposite enantioselectivity. A mechanistic proposal governed by hydrogen bonding is presented.",

author = "Sakie Kawahara and Ayako Nakano and Tomoyuki Esumi and Yoshiharu Iwabuchi and Susumi Hatakeyama",

year = "2003",

month = aug,

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doi = "10.1021/ol035102j",

language = "English",

volume = "5",

pages = "3103--3105",

journal = "Organic Letters",

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T1 - β-isocupreidine-catalyzed asymmetric Baylis-Hillman reaction of imines

AU - Kawahara, Sakie

AU - Nakano, Ayako

AU - Esumi, Tomoyuki

AU - Iwabuchi, Yoshiharu

AU - Hatakeyama, Susumi

PY - 2003/8/21

Y1 - 2003/8/21

N2 - (Matrix presented) β-Isocupreidine (β-ICD)-catalyzed asymmetric Baylis-Hillman reactions of aromatic imines with 1,1,1,3,3, 3-hexafluoroisopropyl acrylate (HFIPA) give (S)-enriched N-protected-α -methylene-β-amino acid esters. In contrast to the corresponding aldehydes, imines show the opposite enantioselectivity. A mechanistic proposal governed by hydrogen bonding is presented.

AB - (Matrix presented) β-Isocupreidine (β-ICD)-catalyzed asymmetric Baylis-Hillman reactions of aromatic imines with 1,1,1,3,3, 3-hexafluoroisopropyl acrylate (HFIPA) give (S)-enriched N-protected-α -methylene-β-amino acid esters. In contrast to the corresponding aldehydes, imines show the opposite enantioselectivity. A mechanistic proposal governed by hydrogen bonding is presented.

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EP - 3105

JO - Organic Letters

JF - Organic Letters

IS - 17

ER -

β-isocupreidine-catalyzed asymmetric Baylis-Hillman reaction of imines

Abstract

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