| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1345391 | Tetrahedron: Asymmetry | 2015 | 8 Pages |
An enantioselective and diastereoselective synthesis of γ,δ-unsaturated carboxylic acids by palladium-catalyzed carbon alkylation of bis(trimethylsilyl)ketene acetals with (E)-1,3-diphenylpropenyl acetate was developed. These acids could be efficiently turned into new γ- or δ-halolactones containing multiple stereocenters using a halolactonization protocol. The stereochemistry of these acids was established by X-ray analysis after derivatization to the corresponding amide with (R)-(+)-1-phenylethylamine.
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(E)-1-(1,3-Diphenylallyl)cyclohexanecarboxylic acidC22H25O2[α]D25 = +32.7 (c 0.00661, CHCl3)Source of chirality: (R)-BINAPAbsolute configuration: (3S)
(E)-1-(1,3-Diphenylallyl)cyclopentanecarboxylic acidC20H20O2[α]D25 = +12.0 (c 0.0102, CHCl3)Source of chirality: (R)-BINAPAbsolute configuration: (3S)
(E)-1-(1,3-Diphenylallyl)cyclobutanecarboxylic acidC20H20O2[α]D25 = −1.8 (c 0.0112, CHCl3)Source of chirality: (R)-BINAPAbsolute configuration: (3S)
(E)-2,2-Dimethyl-3,5-diphenylpent-4-enoic acidC19H20O2[α]D25 = +45.0 (c 0.01, CHCl3)Source of chirality: (R)-BINAPAbsolute configuration: (3S)
(E)-2,2,3,5-Tetraphenylpent-4-enoic acidC29H25O2[α]D25 = +64.1 (c 0.01, CHCl3)Source of chirality: (R)-BINAPAbsolute configuration: (3S)
(E)-2-Isopropyl-3,5-diphenylpent-4-enoic acidC20H22O2[α]D25 = −13.3 (c 0.01, CHCl3)Source of chirality: (R)-BINAPAbsolute configuration: (3S)
(E)-2-(tert-Butyl)-3,5-diphenylpent-4-enoic acidC21H24O2[α]D25 = −42.6 (c 0.0053, CHCl3)Source of chirality: (R)-BINAPAbsolute configuration: (2S,3S)
(E)-2-Ethyl-3,5-diphenylpent-4-enoic acidC19H21O2[α]D25 = +4.8 (c 0.01, CHCl3)Source of chirality: (R)-BINAPAbsolute configuration: (2S,3S)
(E)-2,3,5-Triphenylpent-4-enoic acidC23H21O2[α]D25 = −78.9 (c 0.0053, CHCl3)Source of chirality: (R)-BINAPAbsolute configuration: (2S,3S)
(E)-2-(4-Methoxyphenyl)-3,5-diphenylpent-4-enoic acidC24H23O3[α]D25 = −41.1 (c 0.0053, CHCl3)Source of chirality: (R)-BINAPAbsolute configuration: (2S,3S)
(E)-2-Isopropyl-3,5-diphenyl-N-((R)-1-phenylethyl)pent-4-enamideC28H32N1O1[α]D25 = +51.9 (c 0.053, CHCl3)Source of chirality: (R)-BINAP and precursorAbsolute configuration: (2S,3S,21R)
5-(Bromo(phenyl)methyl)-3,3-dimethyl-4-phenyldihydrofuran-2(3H)-oneC19H20BrO2[α]D25 = +61.6 (c 0.01, CHCl3)Source of chirality: (R)-BINAPAbsolute configuration: (4R,5S,20R)
5-I(phenyl)methyl)-3,3-dimethyl-4-phenyldihydrofuran-2(3H)-oneC19H20IO2[α]D25 = +17.3 (c 0.04, CHCl3)Source of chirality: (R)-BINAPAbsolute configuration: (4R,5S,20R)
5-Bromo-3,3-dimethyl-4,6-diphenyltetrahydro-2H-pyran-2-oneC19H20BrO2[α]D25 = +55.3 (c 0.01, CHCl3)Source of chirality: (R)-BINAP
