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Issue 26, 2012

Direct catalytic asymmetric synthesis of highly functionalized (2-ethynylphenyl)alcohols via Barbas–List aldol reaction: scope and synthetic applications

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Abstract

A high-yielding asymmetric synthesis of functionalized (2-ethynylphenyl)alcohols 5/6 with good diastereo- and enantioselectivities was achieved by Barbas–List aldol (BLA) reaction of 2-alkynylbenzaldehydes 1 with various ketones 2 in the presence of trans-4-OH-L-proline or L-prolinamide derivative 3/4 as catalyst at the ambient temperature or −35 °C. This method also gives first time access to the novel double aldol addition compounds 6, which are of medicinal importance. Chiral functionalized (2-ethynylphenyl)alcohols 5/6 were transformed into acyclic and cyclic 1,4-triazoles 8/9 and cis-1,3-diols 10 in good yields with high selectivity through double click-reaction and Lewis acid-mediated NaBH4 reduction respectively. Chiral products 8–10 may become good ligands and inhibitors in medicinal chemistry.

Graphical abstract: Direct catalytic asymmetric synthesis of highly functionalized (2-ethynylphenyl)alcohols via Barbas–List aldol reaction: scope and synthetic applications

Supplementary files

Article information


Submitted
15 Mar 2012
Accepted
25 Apr 2012
First published
25 Apr 2012

Org. Biomol. Chem., 2012,10, 5094-5101
Article type
Paper

Direct catalytic asymmetric synthesis of highly functionalized (2-ethynylphenyl)alcohols via Barbas–List aldol reaction: scope and synthetic applications

D. B. Ramachary, R. Mondal and R. Madhavachary, Org. Biomol. Chem., 2012, 10, 5094 DOI: 10.1039/C2OB25563D

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