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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Detalles Bibliográficos
Autores principales: Yin, Bo, Ye, Dong-Nai, Yu, Kai-Hui, Liu, Liang-Xian
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Molecular Diversity Preservation International 2010
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6257261/
https://www.ncbi.nlm.nih.gov/pubmed/20428078
http://dx.doi.org/10.3390/molecules15042771
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author Yin, Bo
Ye, Dong-Nai
Yu, Kai-Hui
Liu, Liang-Xian
author_facet Yin, Bo
Ye, Dong-Nai
Yu, Kai-Hui
Liu, Liang-Xian
author_sort Yin, Bo
collection PubMed
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.
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spelling pubmed-62572612018-11-30 A General and Simple Diastereoselective Reduction by l-Selectride: Efficient Synthesis of Protected (4S,5S)-Dihydroxy Amides Yin, Bo Ye, Dong-Nai Yu, Kai-Hui Liu, Liang-Xian Molecules Article 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. Molecular Diversity Preservation International 2010-04-16 /pmc/articles/PMC6257261/ /pubmed/20428078 http://dx.doi.org/10.3390/molecules15042771 Text en © 2010 by the authors; licensee Molecular Diversity Preservation International, Basel, Switzerland. This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Yin, Bo
Ye, Dong-Nai
Yu, Kai-Hui
Liu, Liang-Xian
A General and Simple Diastereoselective Reduction by l-Selectride: Efficient Synthesis of Protected (4S,5S)-Dihydroxy Amides
title 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_short 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
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6257261/
https://www.ncbi.nlm.nih.gov/pubmed/20428078
http://dx.doi.org/10.3390/molecules15042771
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