A novel one-pot reaction involving organocopper-mediated reduction/transmetalation/asymmetric alkylation, leading to the diastereoselective synthesis of functionalized (Z)-fluoroalkene dipeptide isosteres

Tetsuo Narumi; Ayumu Niida; Kenji Tomita; Shinya Oishi; Akira Otaka; Hiroaki Ohno; Nobutaka Fujii

doi:10.1039/B608596B

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A novel one-pot reaction involving organocopper-mediated reduction/transmetalation/asymmetric alkylation, leading to the diastereoselective synthesis of functionalized (Z)-fluoroalkene dipeptide isosteres†

Tetsuo Narumi,^a Ayumu Niida,^a Kenji Tomita,^a Shinya Oishi,^a Akira Otaka,^ab Hiroaki Ohno^a and Nobutaka Fujii*^a

Author affiliations

* Corresponding authors

^a Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Japan
E-mail: nfujii@pharm.kyoto-u.ac.jp

^b Graduate School of Pharmaceutical Sciences, The University of Tokushima, Japan

Abstract

By a novel one-pot reaction sequence involving consecutive organocopper-mediated reduction, transmetalation and asymmetric alkylation, a highly diastereoselective synthesis of functionalized (Z)-fluoroalkene dipeptide isosteres was achieved in good to excellent yields.

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Supplementary files

Experimental procedures, spectral data and analytical data for 12a, and copies of ¹H and ¹³C NMR spectra for all new compounds PDF (1004K)

Article information

DOI: https://doi.org/10.1039/B608596B
Article type: Communication
Submitted: 16 Jun 2006
Accepted: 14 Sep 2006
First published: 28 Sep 2006

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Chem. Commun., 2006, 4720-4722

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A novel one-pot reaction involving organocopper-mediated reduction/transmetalation/asymmetric alkylation, leading to the diastereoselective synthesis of functionalized (Z)-fluoroalkene dipeptide isosteres

T. Narumi, A. Niida, K. Tomita, S. Oishi, A. Otaka, H. Ohno and N. Fujii, Chem. Commun., 2006, 4720 DOI: 10.1039/B608596B

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Chemical Communications

A novel one-pot reaction involving organocopper-mediated reduction/transmetalation/asymmetric alkylation, leading to the diastereoselective synthesis of functionalized (Z)-fluoroalkene dipeptide isosteres†

Abstract

Supplementary files

Article information

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A novel one-pot reaction involving organocopper-mediated reduction/transmetalation/asymmetric alkylation, leading to the diastereoselective synthesis of functionalized (Z)-fluoroalkene dipeptide isosteres

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