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

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; in revised form: 24 March 2010 / Accepted: 12 April 2010 / Published: 16 April 2010
(This article belongs to the Special Issue Asymmetric Synthesis)
PDF Full-text Download PDF Full-Text [194 KB, uploaded 16 April 2010 11:31 CEST]
Abstract: 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

Article Statistics

Load and display the download statistics.

Citations to this Article

Cite This Article

MDPI and ACS Style

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.

AMA Style

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(4):2771-2781.

Chicago/Turabian Style

Yin, Bo; Ye, Dong-Nai; Yu, Kai-Hui; Liu, Liang-Xian. 2010. "A General and Simple Diastereoselective Reduction by L-Selectride: Efficient Synthesis of Protected (4S,5S)-Dihydroxy Amides." Molecules 15, no. 4: 2771-2781.

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert