| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1346063 | Tetrahedron: Asymmetry | 2012 | 9 Pages |
A variety of chiral tert-butanesulfinylphosphine ligands were prepared and applied to the palladium-catalyzed asymmetric allylic etherification of 1,3-diphenylpropenyl acetate with alcohols. Excellent yields and moderate enantioselectivities were obtained. The absolute configuration of the etherification products was evidently switched only through the position change of the substituent on the P-aryl groups.
Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide
(R)-(2-(tert-Butylsulfinyl)-6-methoxyphenyl)diphenylphosphineC23H25O2PS[α]D20=+179 (c 0.1, CHCl3)Source of chirality: (R)-1-(tert-butylsulfinyl)-3-methoxybenzeneAbsolute configuration: (R)
(R)-(2-(tert-Butylsulfinyl)-5-methoxyphenyl)di-o-tolylphosphineC25H29O2PS[α]D20=+267 (c 0.134, CHCl3)Source of chirality: (R)-1-(tert-butylsulfinyl)-4-methoxybenzeneAbsolute configuration: (R)
(R)-(2-(tert-Butylsulfinyl)phenyl)di-o-tolylphosphineC24H27OPS[α]D20=+351 (c 0.146, CHCl3)Source of chirality: (R)-(tert-butylsulfinyl)benzeneAbsolute configuration: (R)
(R)-(2-(tert-Butylsulfinyl)phenyl)di-m-tolylphosphineC24H27OPS[α]D20=+237 (c 0.152, CHCl3)Source of chirality: (R)-(tert-butylsulfinyl)benzeneAbsolute configuration: (R)
(R)-(2-(tert-Butylsulfinyl)phenyl)di-p-tolylphosphineC24H27OPS[α]D20=+289 (c 0.31, CHCl3)Source of chirality: (R)-(tert-butylsulfinyl)benzeneAbsolute configuration: (R)
(R)-(2-(tert-Butylsulfinyl)phenyl)bis(2-fluorophenyl)phosphineC22H21F2OPS[α]D20=+307 (c 0.248, CHCl3)Source of chirality: (R)-(tert-butylsulfinyl)benzeneAbsolute configuration: (R)
(R)-(2-(tert-Butylsulfinyl)phenyl)bis(4-fluorophenyl)phosphineC22H21F2OPS[α]D20=+255 (c 0.208, CHCl3)Source of chirality: (R)-(tert-butylsulfinyl)benzeneAbsolute configuration: (R)
(R)-(2-(tert-Butylsulfinyl)phenyl)bis(4-methoxyphenyl)phosphineC24H27O3PS[α]D20=+241 (c 0.182, CHCl3)Source of chirality: (R)-(tert-butylsulfinyl)benzeneAbsolute configuration: (R)
(R,E)-(3-(Benzyloxy)prop-1-ene-1,3-diyl)dibenzeneC22H20O[α]D20=-13 (c 0.202, toluene)Source of chirality: (R)-(2-(tert-butylsulfinyl)phenyl)di-p-tolylphosphineAbsolute configuration: (R)
(R,E)-(3-((2-Fluorobenzyl)oxy)prop-1-ene-1,3-diyl)dibenzeneC22H19FO[α]D20=-8 (c 0.158, toluene)Source of chirality: (R)-(2-(tert-butylsulfinyl)phenyl)di-p-tolylphosphineAbsolute configuration: (R)
(R,E)-(3-((2-Chlorobenzyl)oxy)prop-1-ene-1,3-diyl)dibenzeneC22H19ClO[α]D20=-13 (c 0.138, toluene)Source of chirality: (R)-(2-(tert-butylsulfinyl)phenyl)di-p-tolylphosphineAbsolute configuration: (R)
(R,E)-(3-((3-Chlorobenzyl)oxy)prop-1-ene-1,3-diyl)dibenzeneC22H19ClO[α]D20=-12 (c 0.142, toluene)Source of chirality: (R)-(2-(tert-butylsulfinyl)phenyl)di-p-tolylphosphineAbsolute configuration: (R)
(R,E)-(3-((3-Bromobenzyl)oxy)prop-1-ene-1,3-diyl)dibenzeneC22H19 BrO[α]D20=-10 (c 0.168, toluene)Source of chirality: (R)-(2-(tert-butylsulfinyl)phenyl)di-p-tolylphosphineAbsolute configuration: (R)
(R,E)-(3-((4-Bromobenzyl)oxy)prop-1-ene-1,3-diyl)dibenzeneC22H19 BrO[α]D20=-19 (c 0.222, toluene)Source of chirality: (R)-(2-(tert-butylsulfinyl)phenyl)di-p-tolylphosphineAbsolute configuration: (R)
(R,E)-(3-((2-Methylbenzyl)oxy)prop-1-ene-1,3-diyl)dibenzeneC23H22O[α]D20=-7 (c 0.144, toluene)Source of chirality: (R)-(2-(tert-butylsulfinyl)phenyl)di-p-tolylphosphineAbsolute configuration: (R)
(R,E)-(3-((4-Methylbenzyl)oxy)prop-1-ene-1,3-diyl)dibenzeneC23H22O[α]D20=-13 (c 0.244, toluene)Source of chirality: (R)-(2-(tert-butylsulfinyl)phenyl)di-p-tolylphosphineAbsolute configuration: (R)
(R,E)-(3-((3-Methoxybenzyl)oxy)prop-1-ene-1,3-diyl)dibenzeneC23H22O2[α]D20=-15 (c 0.168, toluene)Source of chirality: (R)-(2-(tert-butylsulfinyl)phenyl)di-p-tolylphosphineAbsolute configuration: (R)
(R,E)-(3-((3,4-Dimethoxybenzyl)oxy)prop-1-ene-1,3-diyl)dibenzeneC24H24O3[α]D20=-19 (c 0.14, toluene)Source of chirality: (R)-(2-(tert-butylsulfinyl)phenyl)di-p-tolylphosphineAbsolute configuration: (R)
(R,E)-(3-((4-Nitrobenzyl)oxy)prop-1-ene-1,3-diyl)dibenzeneC22H19NO3[α]D20=-26 (c 0.122, toluene)Source of chirality: (R)-(2-(tert-butylsulfinyl)phenyl)di-p-tolylphosphineAbsolute configuration: (R)
(R,E)-1-(((1,3-Diphenylallyl)oxy)methyl)naphthaleneC26H22O[α]D20=-17 (c 0.176, toluene)Source of chirality: (R)-(2-(tert-butylsulfinyl)phenyl)di-p-tolylphosphineAbsolute configuration: (R)
((R,E)-3-(Cinnamyloxy)prop-1-ene-1,3-diyl)dibenzeneC24H22O[α]D20=-19 (c 0.122, toluene)Source of chirality: (R)-(2-(tert-butylsulfinyl)phenyl)di-p-tolylphosphineAbsolute configuration: (R)
(R,E)-2-(((1,3-Diphenylallyl)oxy)methyl)furanC20H18O2[α]D20=-4 (c 0.128, toluene)Source of chirality: (R)-(2-(tert-butylsulfinyl)phenyl)di-p-tolylphosphineAbsolute configuration: (R)
(R,E)-2-(((1,3-Diphenylallyl)oxy)methyl)thiopheneC20H18OS[α]D20=-20 (c 0.138, toluene)Source of chirality: (R)-(2-(tert-butylsulfinyl)phenyl)di-p-tolylphosphineAbsolute configuration: (R)
(S,E)-2-(((1,3-Diphenylallyl)oxy)methyl)pyridineC21H19NO[α]D20=+14 (c 0.152, toluene)Source of chirality: (R)-(2-(tert-butylsulfinyl)phenyl)di-o-tolylphosphineAbsolute configuration: (S)
(R,E)-(3-Methoxyprop-1-ene-1,3-diyl)dibenzeneC16H16O[α]D20=+9 (c 0.164, toluene)Source of chirality: (R)-(2-(tert-butylsulfinyl)phenyl)di-p-tolylphosphineAbsolute configuration: (R)
(S,E)-Dimethyl 2-(1,3-diphenylallyl)malonateC20H20O4[α]D20=-12 (c 0.268, CHCl3)Source of chirality: (R)-(2-(tert-butylsulfinyl)phenyl)di-p-tolylphosphineAbsolute configuration: (S)
(S,E)-N-Benzyl-1,3-diphenylprop-2-en-1-amineC22H21N[α]D20=+14 (c 0.194, CHCl3)Source of chirality: (R)-(2-(tert-butylsulfinyl)phenyl)di-o-tolylphosphineAbsolute configuration: (S)
