Asymmetric Synthesis of Arylalanines via Asymmetric Aza‐Darzens (ADZ) Reaction.

Abstract

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Next Generation of Fluorine-Containing Pharmaceuticals, Compounds Currently in Phase II–III Clinical Trials of Major Pharmaceutical Companies: New Structural Trends and Therapeutic Areas

“…A favorable upstream material for the preparation of 389 is 4-fluorobenzaldehyde ( 400 ), which in turn can be obtained by halogen-exchange fluorination of 4-chlorobenzaldehyde ( 399 ) with KF in the presence of tetraphenylphosphonium bromide and 18-crown-6 (or polyethylene glycol dimethyl ether) (Scheme ). − The reaction of 400 with hippuric acid ( N -benzoylglycine) provided racemic N -benzoylamino acid 401 , and eventually the optically pure amino acid is accessible by enzymatic resolution. , Alternatively, asymmetric synthesis is another approach for preparing 4-fluoro-( R )-Phe ( 389 ) from 400 . − …”

Phase Transfer Catalysis of Henry and Darzens Reactions

“…The formation of a carbon-carbon bond is the fundamental reaction in organic synthesis [1][2][3][4][5]. To this respect, Henry [6][7][8][9] and Darzens [10][11][12] reactions can be considered as excellent tools to give access to multifunctional compounds [13,14]. The Darzens reaction gives α,β-epoxy carbonyl compounds, whereas the Henry reaction leads to nitroaldols.…”