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Tetrahedron Letters
Volume 39, Issue 40, 1 October 1998, Pages 7365-7368
 
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doi:10.1016/S0040-4039(98)01597-4    How to Cite or Link Using DOI (Opens New Window)
Copyright © 1998 Published by Elsevier Science Ltd.

The first asymmetric carbonylation of 1-(6′-methoxy-2′-naphthyl)ethanol to the methyl ester of (S)-naproxen

Bao-Han Xie, Chun-Gu Xia, Shi-Jie Lu, Ke-Jun Chen, Yuan Kou and Yuan-Qi Yin*

State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, P.R.China

Received 17 January 1998; 
accepted 20 April 1998. 
Available online 2 November 1998.

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Abstract

1-(6′-Methoxy-2′-naphthyl)ethanol is asymmetrically carbonylated to the methyl ester of (S)-naproxen in a PdCl2---CuCl2-DDPPI (DDPPI: 1,4:3,6-dianhydro-2,5-dideoxy-2,5-bis(diphenylphosphino)-L-iditol) catalytic system with a chemical yield of 90% and an optical yield of 81% e.e.. The reaction was carried out in ethyl methyl ketone under 100°C and 8 MPa of CO for 24–48h.

Graphical Abstract

1-(6′-methoxy-2′-naphthyl)ethanol asymmetrically carbonylates to methyl ester of (S)-naproxen in a PdCl2---CuCl2---DDPPI (DDPPI: 1,4:3,6-dianhydro-2,5-dideoxy-2,5-bis(diphenylphosphino)-l-iditol) catalytic system.


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Tetrahedron Letters
Volume 39, Issue 40, 1 October 1998, Pages 7365-7368
 
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