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

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 mann...

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Bibliographic Details
Published inSynlett Vol. 26; no. 1; pp. 55 - 58
Main Authors Tarui, Atsushi, Miyata, Erina, Tanaka, Ayumi, Sato, Kazuyuki, Omote, Masaaki, Ando, Akira
Format Journal Article
LanguageEnglish
Published Stuttgart · New York Georg Thieme Verlag 01.01.2015
Thieme Medical Publishers
Subjects
Chemistry
Chemistry, Organic
cluster
Physical Sciences
Science & Technology
cross-coupling
nickel
9-BBN
β-lactam
fluorine
ARYLATIONS
ASYMMETRIC-SYNTHESIS
beta-lactam
CHOLESTEROL ABSORPTION
MEDICINAL CHEMISTRY
ALKYL FLUORIDES
CROSS-COUPLINGS
BOND
ELECTROPHILES
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Summary: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.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0034-1379637