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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 43, 2013 - Issue 21
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Original Articles

Asymmetric Synthesis of Unnatural Amino Acids and Tamsulosin Chiral Intermediate

, , , , &
Pages 2892-2897 | Received 17 Oct 2012, Published online: 25 Jul 2013
 

Abstract

An efficient and enantioselective hydrogenation of N-acetylamino phenyl acrylic acids was successfully developed by using ruthenium catalyst. This methodology is important in the field of pharmaceuticals and provides a new process for the preparation of unnatural amino acids and tamsulosin chiral intermediate.

[Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications® for the following free supplemental resource: Full experimental and spectral details.]

GRAPHICAL ABSTRACT

ACKNOWLEDGMENT

The authors are grateful to Suven Life Sciences management for allowing them to publish these results.

Notes

a Isolated yields for two stages (1 to 3).

a Conversion was determined by Citation 1 H NMR spectra.

b ee were determined by chiral HPLC. Chiral ratio of the products was 81:19 (for bromo 4d) to 96:4 (for fluoro 4b).

c Isolated yield.

a Conversion was determined by TLC.

b ee were determined by chiral HPLC. Chiral ratio of the products was 85.9:14.1 (for 5i) to 99.7:0.23 (for bromo 5d).

c Isolated yield.

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