Synlett 2015; 26(01): 55-58
DOI: 10.1055/s-0034-1379637
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© Georg Thieme Verlag Stuttgart · New York

Stereoselective Suzuki Coupling Reaction of an α-Bromo-α-fluoro-β-lactam

Atsushi Tarui
Faculty of Pharmaceutical Sciences, Setsunan University, 45-1, Nagaotoge-cho, Hirakata, Osaka 573-0101, Japan   Email: aando@pharm.setsunan.ac.jp   Email: tarui-a@pharm.setsunan.ac.jp
,
Erina Miyata
Faculty of Pharmaceutical Sciences, Setsunan University, 45-1, Nagaotoge-cho, Hirakata, Osaka 573-0101, Japan   Email: aando@pharm.setsunan.ac.jp   Email: tarui-a@pharm.setsunan.ac.jp
,
Ayumi Tanaka
Faculty of Pharmaceutical Sciences, Setsunan University, 45-1, Nagaotoge-cho, Hirakata, Osaka 573-0101, Japan   Email: aando@pharm.setsunan.ac.jp   Email: tarui-a@pharm.setsunan.ac.jp
,
Kazuyuki Sato
Faculty of Pharmaceutical Sciences, Setsunan University, 45-1, Nagaotoge-cho, Hirakata, Osaka 573-0101, Japan   Email: aando@pharm.setsunan.ac.jp   Email: tarui-a@pharm.setsunan.ac.jp
,
Masaaki Omote
Faculty of Pharmaceutical Sciences, Setsunan University, 45-1, Nagaotoge-cho, Hirakata, Osaka 573-0101, Japan   Email: aando@pharm.setsunan.ac.jp   Email: tarui-a@pharm.setsunan.ac.jp
,
Akira Ando*
Faculty of Pharmaceutical Sciences, Setsunan University, 45-1, Nagaotoge-cho, Hirakata, Osaka 573-0101, Japan   Email: aando@pharm.setsunan.ac.jp   Email: tarui-a@pharm.setsunan.ac.jp
› Author Affiliations
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Publication History

Received: 22 September 2014

Accepted after revision: 09 November 2014

Publication Date:
28 November 2014 (online)


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Abstract

A new strategy has been developed for the synthesis of α-aryl-α-fluoro-β-lactams via the Suzuki cross-coupling of α-bromo-α-fluoro-β-lactam with a range of different aryl-(9-BBN) reagents. This method provides facile access to multisubstituted α-fluoro-β-lactams in a diastereoselective manner. The synthetic utility of α-bromo-α-fluoro-β-lactam has been demonstrated by the arylation of α-bromo-α-fluoro-β-lactam.

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