Synthesis of optically active 4-hydroxymandelic acid and derivatives via Regio- and Stereoselective Friedel-Crafts alkylation.

doi:10.1016/S0957-4166(00)82212-0

Tetrahedron: Asymmetry

Volume 4, Issue 12, 1993, Pages 2411-2414

https://doi.org/10.1016/S0957-4166(00)82212-0 Get rights and content

Abstract

Optically active 4-hydroxymandelic esters were prepared in good yields and very high diastereoselectivity (up to 96% d.e.) via para-hydroxyalkylation of phenolic ethers. Enantiomeric pure 4-hydroxymandelic acid is available by hydrolysis.

Synthesis of 4-hydroxymandelic acid 6 and derivatives 3 and 4 via hydroxylation of 1.

References (19)

G. Casiraghi et al.
J. Chem. Soc.
(1978)
E.W. Collington et al.
Tetrahedron Lett.
(1985)
a)The Merck Index, 11ed., Centennial Edition, Rahway, N.Y.,...D.J. Triggle
D. Bounzard et al.
Chem. Abstr.
(1978)
H. Iwagami et al.
Bull. Chem. Soc. Jpn.
(1990)
J. Mills et al.
Chem. Abstr.
(1980)
P.N. Edwards et al.
Chem. Abstr.
(1983)
K. Izawa et al.
Chem. Abstr.
(1986)
A. Schouteeten et al.
Chem. Abstr.
(1980)
Chem. Abstr.
(1982)
Y. Honda et al.
Chem. Abstr.
(1990)

There are more references available in the full text version of this article.

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CommunicationsSynthesis of optically active 4-hydroxymandelic acid and derivatives via Regio- and Stereoselective Friedel-Crafts alkylation.

Abstract

J. Chem. Soc.

Tetrahedron Lett.

Chem. Abstr.

Bull. Chem. Soc. Jpn.

Chem. Abstr.

Chem. Abstr.

Chem. Abstr.

Chem. Abstr.

Chem. Abstr.

Chem. Abstr.

Communications
Synthesis of optically active 4-hydroxymandelic acid and derivatives via Regio- and Stereoselective Friedel-Crafts alkylation.