| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1346176 | Tetrahedron: Asymmetry | 2012 | 8 Pages |
The reaction of (E)-1,2-diphenylethenylboronic acid 1 with 2-cyclohexenone in the presence of a chiral diene/rhodium catalyst (5 mol %) gave 3-[2-((E)-2-phenylethenyl)phenyl]cyclohexanone in 99% yield with 98.7% ee; the catalytic cycle involves a 1,4-rhodium shift from a 2-phenylethenylrhodium to an ortho-alkenylphenylrhodium intermediate. In the reaction of 1 with (E)-1-phenyl-2-buten-1-one, either the tandem 1,4-shift/arylation product or the direct alkenylation product is formed selectively by an appropriate choice of chiral diene ligand.
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(R)-3-[2-((E)-2-Phenylethenyl)phenyl]cyclohexanoneC20H20OEnantiomeric excess: 99% ee[α]D20=+116.4 (c 0.90, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R)
(R)-3-[5-Methyl-2-((E)-2-(4-methylphenyl)ethenyl)phenyl]cyclohexanoneC22H24OEnantiomeric excess: 99% ee[α]D20=+138.9 (c 0.57, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R)
(S)-1-Phenyl-3-[2-((E)-2-phenylethenyl)phenyl]butan-1-oneC24H22OEnantiomeric excess: 95% ee[α]D20=-82.7 (c 0.77, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)
(S,E)-3-Methyl-1,4,5-triphenylpent-4-en-1-oneC24H22OEnantiomeric excess: 94% ee[α]D20=-23.1 (c 1.13, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)
(R)-3-[2-((E)-2-Phenylethenyl)phenyl]cyclopentanoneC19H18OEnantiomeric excess: 96% ee[α]D20=+65.3 (c 0.83, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R)
(R)-3-[2-((E)-2-Phenylethenyl)phenyl]cycloheptanoneC21H22OEnantiomeric excess: 95% ee[α]D20=+112.4 (c 0.61, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R)
(S)-1-(4-Methoxyphenyl)-3-[2-((E)-2-phenylethenyl)phenyl]butan-1-oneC25H24O2Enantiomeric excess: 94% ee[α]D20=-102.2 (c 1.08, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)
(S)-1-[4-(Trifluoromethyl)phenyl]-3-[2-((E)-2-phenylethenyl)phenyl]butan-1-oneC25H21F3OEnantiomeric excess: 96% ee[α]D20=-80.9 (c 0.92, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)
C19H20O(S)-4-[2-((E)-2-Phenylethenyl)phenyl]pentan-2-oneEnantiomeric excess: 97% ee[α]D20=-18.9 (c 0.83, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)
(S)-4-[2-((E)-2-Phenylethenyl)phenyl]nonan-2-oneC23H28OEnantiomeric excess: 98% ee[α]D20=-7.4 (c 0.87, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)
(R)-5-Methyl-4-[2-((E)-2-phenylethenyl)phenyl]hexan-2-oneC21H24OEnantiomeric excess: 99% ee[α]D20=-118.4 (c 0.57, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R)
(R)-4-[2-((E)-2-Phenylethenyl)phenyl]tetrahydro-2H-pyran-2-oneC19H18O2Enantiomeric excess: 92% ee[α]D20=+76.4 (c 0.38, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R)
(S)-Methyl 3-[2-((E)-2-phenylethenyl)phenyl]butanoateC19H20O2Enantiomeric excess: 88% ee[α]D20=-41.4 (c 0.90, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)
(R)-2-(3-Oxocyclohexyl)benzaldehydeC13H14O2Enantiomeric excess: 99% ee[α]D20=-2.4 (c 0.62, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R)
(R)-2-(3-Oxocyclopentyl)benzaldehydeC12H12O2Enantiomeric excess: 96% ee[α]D20=+28.3 (c 0.92, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R)
