| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1347989 | Tetrahedron: Asymmetry | 2007 | 7 Pages |
The coupling reaction between 2-p-tolylsulfinyl benzaldehyde and substituted boronic acids catalyzed by Pd2(dba)3·CHCl3 proceeds in a stereoselective manner, demonstrating the efficiency of the sulfinyl group as a chiral inductor. Enantiopure secondary diaryl alcohols become easily accessible by subsequent sulfoxide–lithium exchange.
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(S)-2-(p-Tolylsulfinyl)benzaldehydeC14H12O2[α]D20=-278 (c 1, acetone)
(S)-1-Methoxy-3-(p-tolylsulfinyl)benzeneC14H14O2[α]D20=+49.8 (c 1, acetone)
(S)-2-Methoxy-6-(p-tolylsulfinyl)benzaldehydeC15H14O3S[α]D20=-368 (c 1, acetone)
(R)-(2-Methoxyphenyl)(2-((S)-p-tolylsulfinyl)phenyl)methanolC21H20O3S[α]D20=-127.6 (c 0.5, CHCl3)Source of chirality: enantiomerically pure sulfoxide as inductorAbsolute configuration: (R,(S)S)
(R)-(4-Methoxyphenyl)(2-((S)-p-tolylsulfinyl)phenyl)methanolC21H20O3S[α]D20=-108 (c 0.3, CHCl3)Source of chirality: enantiomerically pure sulfoxide as inductorAbsolute configuration: (R,(S)S)
(R)-(2,6-Dimethoxyphenyl)(2-((S)-p-tolylsulfinyl)phenyl)methanolC22H22O4S[α]D20=-128 (c 0.3, CHCl3)Source of chirality: enantiomerically pure sulfoxide as inductorAbsolute configuration: (R,(S)S)
(R)-o-Tolyl(2-((S)-p-tolylsulfinyl)phenyl)methanolC21H20O2S[α]D20=-216 (c 0.5, CHCl3)Source of chirality: enantiomerically pure sulfoxide as inductorAbsolute configuration: (R,(S)S)
(R)-(2-Methoxy-5-methylphenyl)(2-((S)-p-tolylsulfinyl)phenyl)methanolC22H22O3S[α]D20=-59.6 (c 0.5, CHCl3)Source of chirality: enantiomerically pure sulfoxide as inductorAbsolute configuration: (R,(S)S)
(R)-(2-Methoxynaphthalen-1-yl)(2-((S)-p-tolylsulfinyl)phenyl)methanolC25H22O3S[α]D20=+5.2 (c 0.5, CHCl3)Source of chirality: enantiomerically pure sulfoxide as inductorAbsolute configuration: (R,(S)S)
1,3-Dimethoxy-2-((R)-methoxy(2-((S)-p-tolylsulfinyl)phenyl)methyl)benzeneC23H24O4S[α]D20=-316 (c 0.5, CHCl3)Source of chirality: enantiomerically pure sulfoxide as inductorAbsolute configuration: (R,(S)S)
(S)-1,3-Dimethoxy-2-(methoxy(phenyl)methyl)benzeneC16H18O3[α]D20=-107.5 (c 1, CHCl3)Source of chirality: enantiomerically pure sulfoxide as inductorAbsolute configuration: (S)(S)
(S)-1,3-Dimethoxy-2-(methoxy(phenyl)methyl)benzeneC17H20O3[α]D20=-116.7 (c 0.8, CHCl3)Source of chirality: enantiomerically pure sulfoxide as inductorAbsolute configuration: (S)(S)
