| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1348787 | Tetrahedron: Asymmetry | 2007 | 9 Pages |
The synthesis of a novel series of aminophosphine–oxazoline and phosphoramidite–oxazoline is described. The efficacy of these aminophosphine–oxazoline ligands was investigated in the palladium catalysed asymmetric allylic alkylation of 1,3-diphenylprop-2-enyl acetate leading to a maximum of 38% ee at 64% conversion. Phosphoramidite–oxazoline ligands, however, gave ees of up to 87% at 71% conversion in the same reaction and also proved to be effective in the palladium catalysed asymmetric Suzuki coupling between 2-methylnaphthylboronic acid and 1-bromonaphthalene, leading to a maximum of 46% ee in 54% isolated yield at room temperature.
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2-(N-Benzyl-N-diphenylphosphino-2-aminomethylphenyl)-(4S)-4-methyl- 4,5-dihydrooxazoleC30H29N2OP[α]D20=+88 (c 0.28, CHCl3)Source of chirality: (S)-(+)-2-amino-1-propanolAbsolute configuration: (S)
2-(N-Benzyl-N-diphenylphosphino-2-aminomethylphenyl)-(4S)-4-i-propyl-4,5-dihydrooxazoleC32H33N2OP[α]D20=+114 (c 0.30, CHCl3)Source of chirality: (S)-(+)-2-amino-3-methyl-1-butanolAbsolute configuration: (S)
2-(N-Benzyl-N-diphenylphosphino-2-aminomethylphenyl)-(4S)-4-benzyl-4,5-dihydrooxazoleC36H33N2OP[α]D20=+51 (c 0.30, CHCl3)Source of chirality: (S)-(−)-2-amino-3-phenyl-1-propanolAbsolute configuration: (S)
2-(N-Benzyl-N-(−)-TADDOL-2-aminomethylphenyl)-(4S)-4-methyl-4,5-dihydrooxazoleC49H48N2O5P[α]D20=-121.2 (c 0.33, CHCl3)Source of chirality: (S)-(+)-2-amino-1-propanol; (4R,5R)-2,2-dimethyl-α,α,α′,α′-tetraphenyldioxolane-4,5-dimethanolAbsolute configuration: (S,R,R)
2-(N-Benzyl-N-(−)-TADDOL-2-aminomethylphenyl)-(4S)-4-i-propyl-4,5-dihydrooxazoleC51H51N2O5P[α]D20=-145 (c 0.31, CHCl3)Source of chirality: (S)-(+)-2-amino-3-methyl-1-butanol;(4R,5R)-2,2-dimethyl-α,α,α′,α′-tetraphenyldioxolane-4,5-dimethanolAbsolute configuration: (S,R,R)
2-(N-Benzyl-N-(−)-TADDOL-2-aminomethylphenyl)-(4S)-4-benzyl-4,5-dihydrooxazoleC55H52N2O5P[α]D20=-112 (c 0.28, CHCl3)Source of chirality: (S)-(−)-2-amino-3-phenyl-1-propanol; (4R,5R)-2,2-dimethyl-α,α,α′,α′-tetraphenyldioxolane-4,5-dimethanolAbsolute configuration: (S,R,R)
2-(N-Benzyl-N-(+)-TADDOL-2-aminomethylphenyl)-(4S)-4-methyl-4,5-dihydrooxazoleC49H48N2O5P[α]D20=+97 (c 0.28, CHCl3)Source of chirality: (S)-(+)-2-amino-1-propanol; (4S,5S)-2,2-dimethyl-α,α,α′,α′-tetraphenyldioxolane-4,5-dimethanolAbsolute configuration: (S,S,S)
2-(N-Benzyl-N-(+)-TADDOL-2-aminomethylphenyl)-(4S)-4-i-propyl-4,5-dihydrooxazoleC51H51N2O5P[α]D20=+95 (c 0.29, CHCl3)Source of chirality: (S)-(+)-2-amino-3-methyl-1-butanol; (4S,5S)-2,2-Dimethyl-α,α,α′,α′-tetraphenyldioxolane-4,5-dimethanolAbsolute configuration: (S,S,S)
2-(N-Benzyl-N-(+)-TADDOL-2-aminomethylphenyl)-(4S)-4-benzyl-4,5-dihydrooxazoleC55H52N2O5P[α]D20=+55 (c 0.29, CHCl3);Source of chirality: (S)-(−)-2-amino-3-phenyl-1-propanol; (4S,5S)-2,2-dimethyl-α,α,α′,α′-tetraphenyldioxolane-4,5-dimethanolAbsolute configuration: (S,S,S)
