Article ID Journal Published Year Pages File Type
1348166 Tetrahedron: Asymmetry 2006 6 Pages PDF
Abstract

A series of thiophene mono (oxazoline) N,O-ligands with three sites of diversity were synthesized concisely in two steps from the corresponding thiophene carbonitriles. These ligands were applied to the enantioselective phenyl transfer reaction of aldehydes, resulting in the corresponding chiral diaryl methanol products with excellent yields and moderate to good enantioselectivities.

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(R)-(4-Chlorophenyl)(phenyl)methanolEe = 82%[α]D20=-15.4 (c 0.80, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R)

(R)-(4-Bromophenyl)(phenyl)methanolEe = 72%[α]D25=-16.4 (c 0.87, PhH)Source of chirality: asymmetric synthesisAbsolute configuration: (R)

(R)-(4-Methoxyphenyl)(phenyl)methanolEe = 78%[α]D25=+11.4 (c 0.67, PhH)Source of chirality: asymmetric synthesisAbsolute configuration: (R)

(R)-Phenyl(p-tolyl)methanolEe = 75%[α]D25=+6.1 (c 0.50, PhH)Source of chirality: asymmetric synthesisAbsolute configuration: (R)

(R)-(2-Bromophenyl)(phenyl)methanolEe = 65%[α]D25=+36.1 (c 1.10, acetone)Source of chirality: asymmetric synthesisAbsolute configuration: (R)

(R)-(3-Bromophenyl)(phenyl)methanolEe = 65%[α]D25=-18.1 (c 1.10, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R)

(R)-Naphthalen-2-yl(phenyl)methanolEe = 73%[α]D25=+4.1 (c 0.82, PhH)Source of chirality: asymmetric synthesisAbsolute configuration: (R)

(R)-(2,4-Dichlorophenyl)(phenyl)methanolEe = 60%[α]D25=+4.6 (c 3.35, acetone)Source of chirality: asymmetric synthesisAbsolute configuration: (R)

(S,E)-1,3-Diphenylprop-2-en-1-olEe = 74%[α]D25=-28.1 (c 0.44, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R)

Related Topics
Physical Sciences and Engineering Chemistry Inorganic Chemistry
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