- An efficient synthesis of 1-naphthylbis(oxazoline) and exploration of the scope in asymmetric catalysis
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Both enantiomers of 1-naphthylglycine were obtained in 99% ee by enzymatic resolution of the corresponding racemic amino acid amide, giving access to the novel ligands (R)- and (S)-naphthylbis(oxazoline). Initial studies provided insight into the scope an
- Van Lingen, Hester L.,Van de Mortel, Jeroen K. W.,Hekking, Koen F. W.,Van Delft, Floris L.,Sonke, Theo,Rutjes, Floris P. J. T.
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p. 317 - 324
(2007/10/03)
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- A simple and efficient diastereoselective Strecker synthesis of optically pure α-arylglycines
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A simple and economical method for the synthesis of highly functionalised α-amino nitriles, precursors to α-arylglycines with high optical purity is reported. For this purpose, (R) or (S)-2-amino-2- phenylethanol were used as chiral auxiliaries in a 1,3 Strecker reaction. Reactions were studied with a broad range of reagent systems for the generation of cyano nucleophile. Methodology has been extended for the synthesis of (S)-α-(2-iodo-5-nitrophenyl)glycine, (S)-α-(4- methoxyphenyl)glycine and (R)-β-(4-methoxyphenyl)alanine.
- Dave, Rajesh H.,Hosangadi, Bhaskar D.
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p. 11295 - 11308
(2007/10/03)
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- An Efficient and Practical Synthesis of L-α-Amino Acids Using (R)-Phenylglycinol as a Chiral Auxiliary
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L-α-Amino acids including L-α-arylglycines were conveniently and stereoselectively synthesized via the α-amino carbonitriles given by the Strecker reaction of (R)-2-amino-2-phenylethanol with aldehydes and hydrogen cyanide.The stereoselectivity of these α-amino carbonitriles was thermodynamically controlled.
- Inaba, Takashi,Kozono, Ichiro,Fujita, Makoto,Ogura, Katsuyuki
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p. 2359 - 2365
(2007/10/02)
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- Synthesis of Optically Active Arylglycines by Photolysis of Optically Active (β-Hydroxyamino) Carbene-Chromium(0) Complexes
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Photolysis of chromium complexes having the optically active amino alcohol (1R,2S)-(-)- or (1S,2R)-(+)-2-amino-1,2-diphenylethanol as the amino group produced aryl-substituted oxazinones in good yield with reasonable diastereoselectivity.Facile separation of diastereoisomers followed by mild reductive cleavage produced several arylglycines, having either electron-donating or withdrawing groups on the aromatic ring, in good overall yield and with excellent enantiomeric excess.
- Vernier, Jean-Michel,Hegedus, Louis S.,Miller, David B.
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p. 6914 - 6920
(2007/10/02)
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- Asymmetric synthesis of arylglycines
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The asymmetric synthesis of several arylglycines are reported. The methodology deployed involves either cuprate or Friedel - Crafts couplings to chiral bromoglycinates. The % ee's range from 82 to 94%. Both an oxidative and reductive protocol are employed to unmask the oxazinone chiral auxilliary providing the free α-amino acids.
- Williams,Hendrix
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p. 3723 - 3727
(2007/10/02)
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