26629-33-4

Usage

Synthesis Reference(s)

Tetrahedron Letters, 29, p. 1759, 1988 DOI: 10.1016/S0040-4039(00)82035-3

InChI:InChI=1/C6H11NO3/c1-4(6(9)10-3)7-5(2)8/h4H,1-3H3,(H,7,8)

Upstream product

• 35356-70-8 Methyl 2-acetamidoacrylate 
• 98-86-2 acetophenone 
• 67-56-1 methanol 
• 1359827-55-6 hapalocyclamide 
• 108-24-7 acetic anhydride 
• 67969-82-8 tetrafluoroboric acid diethyl ether 
• 373367-07-8 (SCα)-[Ru((R)-BINAP)(MeCN)(α-acetamidoacrylate(H))](BF4) 
• 373367-07-8 (RCα)-[Ru((R)-BINAP)(MeCN)(α-acetamidoacrylate(H))](BF4) 
• 2206-26-0 [D₃]acetonitrile 

Downstream Products

• 97-69-8 (S)-acetamidoalanine 
• 19914-36-4 Methyl (R)-N-acetylalaninate 
• 19436-52-3 (R)-2-(acetylamino)propanoic acid 
• 5429-56-1 N-Acetamidoacrylic acid 
• 1115-69-1 Ac-DL-Ala 

Relevant academic research and scientific papers

Lipase active site covalent anchoring of Rh(NHC) catalysts: Towards chemoselective artificial metalloenzymes

A Rh(NHC) phosphonate complex reacts with the lipases cutinase and Candida antarctica lipase B resulting in the first (soluble) artificial metalloenzymes formed by covalent active site-directed hybridization. When compared to unsupported complexes, these

Hapalocyclamide: A novel phytotoxic hexapeptide of the cyanobacterium Hapalosiphon sp.

Hapalocyclamide, a novel oxazole-, thiazole- and thiazoline-containing cyclic hexapeptide, was isolated from the terrestrial cyanobacterium Hapalosiphon sp., and which showed phytotoxic activity on lettuce seedling growth. The gross structure of hapalocyclamide was established from spectroscopic data and chemical degradation. The absolute stereochemistry was determined by Marfey's analysis. Hapalocyclamide was established as cyclo-thiazole-l-alanine-oxazole-d-alanine-d-thiazoline-d-phenylalanine.

Stereochemistry at carbon upon protonolysis of a late transition metal-alkyl bond: A reaction of relevance to catalytic enantioselective hydrogenation of olefins

Reaction of [Ru((R)-BINAP)(H)(MeCN)n (acetone)3-n](BF4) (where n = 0-3) (2) with 1 equiv of the olefin substrate methyl α-acetamidoacrylate (MAA) in acetone at room temperature immediately generated a mixture (72:28) of two diastereomers of the complex [Ru((R)-BINAP)(MeCN)(MAA(H))](BF4)(3). The olefin-hydride insertion reaction between 2 and MAA to generate 3 was regioselective, with transfer of the hydride to the β-olefinic carbon and transfer of ruthenium to the α-carbon in both diastereomers of 3. The two diastereomers of 3 differ by the absolute configuration at the α-carbon of MAA(H) ((Scα)-3 and (Rcα)-3). The absolute configuration of the major ((Scα)-3) diastereomer was determined by X-ray diffraction in conjunction with NMR spectroscopic data. Protonolysis of the ruthenium-carbon bond in 3 and in the methyl α-acetamidocinnamate (MAC) analog ([Ru((R)-BINAP)(MeCN)((S)-MAC(H))](BF4)((Scα)-4)) by addition of 2 equiv HBF4·Et2O in CH2 Cl2 at room temperature was not stereospecific and did not occur with β-hydride elimination from the methyl or benzyl groups.