1076-51-3Relevant articles and documents
Novel asymmetric catalytic nucleophilic fluorine heterocyclization reaction system and application thereof in chiral non-natural amino acid module synthesis
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, (2021/07/14)
The invention discloses a novel asymmetric catalytic fluorine heterocyclization reaction system and application thereof. The novel asymmetric catalytic fluorine heterocyclization reaction system provided by the invention comprises a chiral iodine catalyst and etherified boron trifluoride, and is applied to a catalytic asymmetric nucleophilic fluorine heterocyclization reaction of unsaturated amide; a fluoro oxazine derivative is obtained through treatment after the reaction; and the obtained fluoro oxazine derivative is subjected to hydrolysis and oxidation reaction to obtain the chiral non-natural amino acid. The reaction system provided by the invention has the following advantages: etherified boron trifluoride is used as a fluorine reagent, is cheap and easy to obtain, and has good stability and low toxicity; the reaction conditions are mild; the chiral iodine catalyst is simple to prepare and does not need a complex ligand; the system is environment-friendly and free of heavy metal pollution and precious metal waste; the obtained product is a fluoro oxazine derivative active molecular structure unit with two chiral centers; chiral non-natural amino acid can be obtained through conversion reaction of the product; and the chemical selectivity and stereoselectivity of the reaction are good, and the yield and optical purity are high.
Organocatalytic asymmetric transferhydrogenation of β-nitroacrylates: Accessing β2-amino acids
Martin, Nolwenn J. A.,Cheng, Xu,List, Benjamin
supporting information; experimental part, p. 13862 - 13863 (2009/02/06)
We describe a highly efficient and enantioselective Hantzsch ester mediated conjugate reduction of β-nitroacrylates that is catalyzed by a Jacobsen thiourea catalyst as a key step in a new route to optically active β2-amino acids. Copyright
Catalytic enantioselective synthesis of β2-amino acids
Davies, Huw M. L.,Venkataramani, Chandrasekar
, p. 2197 - 2199 (2007/10/03)
A very direct approach for the synthesis of β-amino esters is provided by catalytic asymmetric C-H activation by means of carbenoid-induced C-H insertion (see scheme; Boc = butyloxycarbonyl; TFA = trifluoroacetic acid). The reactions described herein represent the first regioselective intermolecular C-H insertions occurring at a methyl site.