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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

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 3.0).

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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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