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Molecules 2010, 15(4), 2771-2781; doi:10.3390/molecules15042771

A General and Simple Diastereoselective Reduction by L-Selectride: Efficient Synthesis of Protected (4S,5S)-Dihydroxy Amides

, ,  and *
Department of Chemistry and Biology, Ganan Normal University, Ganzhou, Jiangxi 341000, China
* Author to whom correspondence should be addressed.
Received: 18 December 2009 / Revised: 24 March 2010 / Accepted: 12 April 2010 / Published: 16 April 2010
(This article belongs to the Special Issue Asymmetric Synthesis)
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A general approach to (4S,5S)-4-benzyloxy-5-hydroxy-N-(4-methoxybenzyl) amides 10 based on a diastereoselective reduction of (5S,6RS)-6-alkyl-5-benzyloxy-6-hydroxy-2-piperidinones 6 and their tautomeric ring-opened keto amides 7 is described. The reduction with L-Selectride at -20 °C to room temperature afforded the products 10 in excellent yields and moderate to high syn-diastereoselectivities.
Keywords: L-Selectride; 3-hydroxyglutarimide; (4S,5S)-dihydroxyamide L-Selectride; 3-hydroxyglutarimide; (4S,5S)-dihydroxyamide
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Yin, B.; Ye, D.-N.; Yu, K.-H.; Liu, L.-X. A General and Simple Diastereoselective Reduction by L-Selectride: Efficient Synthesis of Protected (4S,5S)-Dihydroxy Amides. Molecules 2010, 15, 2771-2781.

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