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

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

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 tempera...

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Bibliographic Details
Main Authors: Bo Yin, Dong-Nai Ye, Kai-Hui Yu, Liang-Xian Liu
Format: Article
Language:English
Published: MDPI AG 2010-04-01
Series:Molecules
Subjects:
L-Selectride
3-hydroxyglutarimide
(4S,5S)-dihydroxyamide
Online Access:http://www.mdpi.com/1420-3049/15/4/2771/
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spelling doaj-3be8cceb65d945aaa7c1cb5657d65d712020-11-24T20:54:53ZengMDPI AGMolecules1420-30492010-04-011542771278110.3390/molecules15042771A General and Simple Diastereoselective Reduction by L-Selectride: Efficient Synthesis of Protected (4S,5S)-Dihydroxy AmidesBo YinDong-Nai YeKai-Hui YuLiang-Xian LiuA 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. http://www.mdpi.com/1420-3049/15/4/2771/L-Selectride3-hydroxyglutarimide(4S,5S)-dihydroxyamide
collection DOAJ
language English
format Article
sources DOAJ
author Bo Yin
Dong-Nai Ye
Kai-Hui Yu
Liang-Xian Liu
spellingShingle Bo Yin
Dong-Nai Ye
Kai-Hui Yu
Liang-Xian Liu
A General and Simple Diastereoselective Reduction by L-Selectride: Efficient Synthesis of Protected (4S,5S)-Dihydroxy Amides
Molecules
L-Selectride
3-hydroxyglutarimide
(4S,5S)-dihydroxyamide
author_facet Bo Yin
Dong-Nai Ye
Kai-Hui Yu
Liang-Xian Liu
author_sort Bo Yin
title A General and Simple Diastereoselective Reduction by L-Selectride: Efficient Synthesis of Protected (4S,5S)-Dihydroxy Amides
title_short A General and Simple Diastereoselective Reduction by L-Selectride: Efficient Synthesis of Protected (4S,5S)-Dihydroxy Amides
title_full A General and Simple Diastereoselective Reduction by L-Selectride: Efficient Synthesis of Protected (4S,5S)-Dihydroxy Amides
title_fullStr A General and Simple Diastereoselective Reduction by L-Selectride: Efficient Synthesis of Protected (4S,5S)-Dihydroxy Amides
title_full_unstemmed A General and Simple Diastereoselective Reduction by L-Selectride: Efficient Synthesis of Protected (4S,5S)-Dihydroxy Amides
title_sort general and simple diastereoselective reduction by l-selectride: efficient synthesis of protected (4s,5s)-dihydroxy amides
publisher MDPI AG
series Molecules
issn 1420-3049
publishDate 2010-04-01
description 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.
topic L-Selectride
3-hydroxyglutarimide
(4S,5S)-dihydroxyamide
url http://www.mdpi.com/1420-3049/15/4/2771/
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