- Studies on the aza-Claisen rearrangement of 4,5-dihydroxylated allylic trichloroacetimidates: the stereoselective synthesis of (2R,3S)- and (2S,3S)-2-amino-3,4-dihydroxybutyric acids
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Two new synthetic approaches, involving substrate directed aza-Claisen rearrangements and aza-Claisen rearrangements mediated by chiral Pd(II) catalysts, have been developed for the stereoselective synthesis of (2R,3S)-2-amino-3,4-dihydroxybutyric acid, a
- Swift, Michael D.,Sutherland, Andrew
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p. 9521 - 9527
(2008/12/22)
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- Porcine pancreatic lipase mediated regio- and stereoselective hydrolysis: Chemoenzymatic synthesis of (2S,3S)-2-amino-3,4-dihydroxybutyric acid
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Porcine pancreatic lipase was used in the chemoenzymatic hydrolysis of 2-azido-3-hydroxy-4-methylcarbonyloxybutyl acetate. The reaction occurred with high regio- and stereoselectivity to give enantiomerically pure (2S,3R)-3-azido-2,4-dihydroxy butyl aceta
- Fadnavis,Sharfuddin,Vadivel
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p. 691 - 693
(2007/10/03)
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- Polyhydroxy amino acid derivatives via β-lactams using enantiospecific approaches and microwave techniques
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Enantiospecific synthesis has been developed for α-hydroxy β-lactams of predictable absolute configuration starting with readily available carbohydrates. Stereospecific approaches and microwave assisted chemical reactions have been utilized for the prepar
- Bose, Ajay K.,Banik, Bimal K.,Mathur, Chandra,Wagle, Dilip R.,Manhas, Maghar S.
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p. 5603 - 5619
(2007/10/03)
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- Diastereoselective strecker reaction of D-glyceraldehyde derivatives. A novel route to (2S,3S)- and (2R,3S)-2-amino-3,4-dihydroxybutyric acid
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Efficient and stereoselective synthetic routes to enantiomerically pure (2S,3S)- and (2S,3S)-2-amino-3,4-dihydroxybutyric acid have been developed using the stereoselective Strecker type reaction of carbonyl compounds derived from appropriately protected
- Cativiela, Carlos,Diaz-De-Villegas, Maria D,Galvez, Jose A.,Garcia, Jose I.
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p. 9563 - 9574
(2007/10/03)
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- Diastereoselective Strecker Reaction of Imines Derived from D-Glyceraldehyde. A New Route to β-hydroxy-α-amino acids
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A diastereoselective Strecker type reaction of imines derived from conveniently protected D-glyceraldehyde has been achieved with good to excellent stereoselectivity through an appropriate choice of the protecting group and reaction conditions.
- Cativiela, Carlos,Diaz-de-Villegas, Maria D.,Galvez, Jose A.
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p. 2859 - 2860
(2007/10/02)
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- Simple Synthesis of L- and D-Vinylglycine (2-Aminobut-3-enoic Acid) and Related Amino Acid
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A three-step synthesis of vinylglycine 1 has been developed using a readily available starting material (but-3-enenitrile 2), based on the Neber rearrangement of the corresponding N-chloroimidate, and using cheap, convenient reagents.Also described is a convenient optical resolution of the N-tert-butoxycarbonyl derivative by papain-catalysed enantioselective esterifucation in a two-phase system.From the optically active amino acid, related amino acids obtained via epoxidation, dihydroxylation and cyclopropanation have been prepared.The related β,γ-unsaturated amino acids (E)-2-aminopent-3-enoic acid 20 and (E)-2-amino-3-methylpent-3-enoic acid 22 have been synthesised using the same approach.
- Hallinan, Keith O.,Crout, David H. G.,Errington, William
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p. 3537 - 3544
(2007/10/02)
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- Structure and Stereochemistry of Three Phytotoxins, Syringomycin, Syringotoxin and Syringostatin, Produced by Pseudomonas syringae pv. syringae
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The structures of two phytotoxins, syringomycin and syringotoxin, produced by Pseudomonas syringae pv. syringae, were determined.Several amino acid residues of syringomycin were different from those in the syringostatins.Syringotoxin B proved to be syringostatin A.The three kinds of phytotoxins showed close structural similarity, and the stereochemistry of their components was deduced and compared.
- Fukuchi, Naoyuka,Isogai, Akira,Nakayama, Jiro,Takayama, Seiji,Yamashita, Shuichi,et al.
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p. 1149 - 1158
(2007/10/02)
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- NEW ENTRY TO SYN-β-HYDROXY-α-AMINO ACIDS
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The intramolecular conjugate addition of allylically situated carbamoyloxy group to properly substituted heteroolefin proceeds with complete 1,2-syn diastereoselectivity, which culminates in a highly stereoselective new synthesis of syn-β-hydroxy-α-amino acids.
- Hirama, Masahiro,Hioki, Hideaki,Ito, Sho
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p. 3125 - 3128
(2007/10/02)
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