Stereoselective Synthesis of Multi-substituted Fluoro-β-lactams and Their Conversion to Fluorinated β-Amino Acid Core

Tarui Atsushi

doi:10.1248/yakushi.15-00201

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多置換フルオロ-β-ラクタム類の立体選択的合成と含フッ素β-アミノ酸骨格への変換
タチカンフルオロ-v-ラクタムルイノリッタイセンタクテキゴウセイトガンフッソv-アミノサンコッカクエノヘンカン

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Multi-substituted β-lactam compounds have not only attracted considerable interest as core structures of pharmaceutical compounds such as antibiotics but also have been used as building blocks for the construction of β-amino acids. Electrophilic β-lactams can be used to enhance essential biological activities. Furthermore, the ring-opening reactions of electrophilic β-lactams can be used to provide facile access to β-amino acids. The introduction of an electronegative fluorine atom to a β-lactam ring to give the corresponding fluoro-β-lactam can be used as an effective strategy for the preparation of electrophilic β-lactams. In this review, we provide a summary of our recent research towards the direct functionalization of fluoro-β-lactams. This review has been divided into four topics, including: 1) the alkylation and hydroxyalkylation of α-bromo-α-fluoro-β-lactams (1); 2) the nickel-catalyzed cross coupling reaction of 1; 3) the asymmetric synthesis of fluoro-β-lactams using chiral ligands; and 4) the utilization of fluoro-β-lactams as highly electrophilic building blocks.<br>

Journal

YAKUGAKU ZASSHI

YAKUGAKU ZASSHI 135 (11), 1245-1253, 2015-11-01

The Pharmaceutical Society of Japan

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