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Diastereoselective allylstannane additions to (S)-5,6-dihydro-2H-5-phenyloxazin-2-one. A concise synthesis of (S)-beta-methylisoleucine.

ABSTRACT: The addition of allyl stannanes to (S)-4,5-dihydro-5-phenyl-2H-oxazinone (3) was achieved under Brønsted acid catalysis to give 2-allylmorpholinones with high diastereoselectivity (up to dr 14.2:1). The product of dimethylallyltributylstannane addition to 3 was converted to l-beta-methylisoleucine, an alpha-amino acid residue found in the complex, biologically active marine-derived peptides polytheonamides A and B, and polydiscamides A-C.

SUBMITTER: Pigza JA

PROVIDER: S-EPMC2837769 | biostudies-literature | 2010 Mar

REPOSITORIES: biostudies-literature

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Diastereoselective allylstannane additions to (S)-5,6-dihydro-2H-5-phenyloxazin-2-one. A concise synthesis of (S)-beta-methylisoleucine.

Pigza Julie A JA Molinski Tadeusz F TF

Organic letters 20100301 6

The addition of allyl stannanes to (S)-4,5-dihydro-5-phenyl-2H-oxazinone (3) was achieved under Brønsted acid catalysis to give 2-allylmorpholinones with high diastereoselectivity (up to dr 14.2:1). The product of dimethylallyltributylstannane addition to 3 was converted to l-beta-methylisoleucine, an alpha-amino acid residue found in the complex, biologically active marine-derived peptides polytheonamides A and B, and polydiscamides A-C. ...[more]

PMID: 20163126

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Project description:BackgroundFor the development of properties in molecular crystals, such as electrical conductivities, magnetic properties, or non-linear optical properties, not only the electronic properties of molecules themselves matter, but also the molecular arrangements in the crystals are very important. Therefore, the design of the crystal structures and the control of molecular arrangements have attracted much attention in recent years. Among various ligands, triazine moieties have been especially interesting because of their biological, pharmacological and medicinal properties.ResultsCrystal structure of 5-Methoxy-5,6-diphenyl-4,5-dihydro-2H-1,2,4-triazine-3-thione is Monoclinic, which consists of space group P21/c with a = 9.699(1), b = 8.500(1), c = 18.044(2) Å, β = 101.290(7)° and Z = 4, R1 = 0.0371 and wR2 = 0.1008 with 2456 reflections (I > 2σ(I)). Intermolecular H bonds between NH groups are acting as donors and S atoms as acceptors. There are also shorted face-to-face as well as edge to face π-π stacking interactions between the parallel aromatic rings. The behavior of solvatochromic of the mentioned compound that involved interhydrogen bonding was investigated by studying its electronic absorption spectra in pure organic solvents of different characters.ConclusionsThe crystal structure of C16H15N3OS, shows the expected face-to-face π-π stacking interactions between aromatic rings of the neighbor chains in this compound. The centroid-centroid distance between the aromatic rings is 3.325 Å. It was found that the monomer of the ligand 5-Methoxy-5,6-diphenyl-4,5-dihydro-2H-1,2,4-triazine-3-thione, further extends into 3D networks via hydrogen bonding and pi-pi stacking interactions. The solvatochromic behavior of the title compound was also investigated by studying its spectra in a selection of different organic solvents. While progressing from the non-polar solvent to the polar one, the main intense band at 310 nm, which is due to the π-π* transition, was red shifted by 13 nm. Thus, the title compound showed positive solvatochromic behavior.

Dataset Information

Diastereoselective allylstannane additions to (S)-5,6-dihydro-2H-5-phenyloxazin-2-one. A concise synthesis of (S)-beta-methylisoleucine.

Publications

Diastereoselective allylstannane additions to (S)-5,6-dihydro-2H-5-phenyloxazin-2-one. A concise synthesis of (S)-beta-methylisoleucine.

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