Direct asymmetric α-amination of cyclic ketones catalyzed by siloxyproline

Yujiro Hayashi, Seiji Aratake, Yoshinaga Imai, Kazuhiro Hibino, Qi Yin Chen, Junichiro Yamaguchi, Tadafumi Uchimaru

Research output: Contribution to journalArticle

34 Citations (Scopus)

Abstract

trans-tert-Butyldimethylsiloxy-l-proline displays greater catalytic activity and affords higher enantioselectivity than the parent proline in the a-amination reaction of carbonyl compounds with azodicarboxylate. A quantum mechanical calculation reveals the structure of the transition state. In the presence of a catalytic amount of siloxyproline and water (3-9 equiv), α-amino carbonyl derivatives, which are important synthetic intermediates, are obtained in good yield and with excellent enantioselectivity.

Original languageEnglish
Pages (from-to)225-232
Number of pages8
JournalChemistry - An Asian Journal
Volume3
Issue number2
DOIs
Publication statusPublished - 2008 Feb 1
Externally publishedYes

Fingerprint

Amination
Enantioselectivity
Ketones
Proline
Carbonyl compounds
Catalyst activity
Display devices
Derivatives
Water
siloxyproline

Keywords

  • Amination
  • Asymmetric synthesis
  • Organocatalysis
  • Proline
  • Siloxyproline

ASJC Scopus subject areas

  • Chemistry(all)
  • Medicine(all)

Cite this

Direct asymmetric α-amination of cyclic ketones catalyzed by siloxyproline. / Hayashi, Yujiro; Aratake, Seiji; Imai, Yoshinaga; Hibino, Kazuhiro; Chen, Qi Yin; Yamaguchi, Junichiro; Uchimaru, Tadafumi.

In: Chemistry - An Asian Journal, Vol. 3, No. 2, 01.02.2008, p. 225-232.

Research output: Contribution to journalArticle

Hayashi, Y, Aratake, S, Imai, Y, Hibino, K, Chen, QY, Yamaguchi, J & Uchimaru, T 2008, 'Direct asymmetric α-amination of cyclic ketones catalyzed by siloxyproline', Chemistry - An Asian Journal, vol. 3, no. 2, pp. 225-232. https://doi.org/10.1002/asia.200700307
Hayashi, Yujiro ; Aratake, Seiji ; Imai, Yoshinaga ; Hibino, Kazuhiro ; Chen, Qi Yin ; Yamaguchi, Junichiro ; Uchimaru, Tadafumi. / Direct asymmetric α-amination of cyclic ketones catalyzed by siloxyproline. In: Chemistry - An Asian Journal. 2008 ; Vol. 3, No. 2. pp. 225-232.
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