Ru-TsDPEN with Formic Acid/Hünig's Base for Asymmetric Transfer Hydrogenation, a Practical Synthesis of Optically Enriched N-Propyl Pantolactam

The Noyori-Ikariya catalysts, Ru-TsDPEN 1 or 2, in combination with HCOOH/Hunig's base (5:2) have been successfully utilized for catalytic asymmetric transfer hydrogenation of alpha-ketopantolactam, and optically enriched N-substituted pantolactam was prepared (S/C = 500, up to 95% ee and 99% c...

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Published in:Journal of organic chemistry 2009-02, Vol.74 (3), p.1411-1414
Main Authors: JI ZHANG, BLAZECKA, Peter G, BRUENDL, Michelle M, YUN HUANG
Format: Article
Language:English
Subjects:
Amines - chemistry
Catalysis
Catalysts: preparations and properties
Chemistry
Ethylenediamines - chemistry
Exact sciences and technology
Formates - chemistry
General and physical chemistry
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Hydrogenation
Lactams - chemical synthesis
Organic chemistry
Organometallic Compounds - chemistry
Preparations and properties
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
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cited_by cdi_FETCH-LOGICAL-c313t-c4b631970ec8dae8c8238c4104f493749276d632c0fa58dbecd0584237bb0c233
cites cdi_FETCH-LOGICAL-c313t-c4b631970ec8dae8c8238c4104f493749276d632c0fa58dbecd0584237bb0c233
container_end_page 1414
container_issue 3
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container_title Journal of organic chemistry
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creator JI ZHANG
BLAZECKA, Peter G
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YUN HUANG
description The Noyori-Ikariya catalysts, Ru-TsDPEN 1 or 2, in combination with HCOOH/Hunig's base (5:2) have been successfully utilized for catalytic asymmetric transfer hydrogenation of alpha-ketopantolactam, and optically enriched N-substituted pantolactam was prepared (S/C = 500, up to 95% ee and 99% conversion in HCOOH/Hunig's base condition). More than 2 kg of this key intermediate 9 has been synthesized efficiently with excellent chemical yield and chiral purity.
doi_str_mv 10.1021/jo802380j
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subjects Amines - chemistry
Catalysis
Catalysts: preparations and properties
Chemistry
Ethylenediamines - chemistry
Exact sciences and technology
Formates - chemistry
General and physical chemistry
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Hydrogenation
Lactams - chemical synthesis
Organic chemistry
Organometallic Compounds - chemistry
Preparations and properties
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
title Ru-TsDPEN with Formic Acid/Hünig's Base for Asymmetric Transfer Hydrogenation, a Practical Synthesis of Optically Enriched N-Propyl Pantolactam
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