Recent Developments in Asymmetric Hydrogenation and Transfer Hydrogenation of Ketones and Imines through Dynamic Kinetic Resolution
Abstract The transition-metal-catalyzed asymmetric transfer hydrogenation (ATH) and asymmetric hydrogenation (AH) of α- and β-substituted ketone or imine derivatives are efficient methods for accessing chiral alcohols or amines bearing up to three stereogenic centers through a dynamic kinetic resolu...
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Veröffentlicht in: | Synthesis (Stuttgart) 2016-08, Vol.48 (16), p.2523-2539 |
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container_title | Synthesis (Stuttgart) |
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creator | Echeverria, Pierre-Georges Ayad, Tahar Phansavath, Phannarath Ratovelomanana-Vidal, Virginie |
description | Abstract
The transition-metal-catalyzed asymmetric transfer hydrogenation (ATH) and asymmetric hydrogenation (AH) of α- and β-substituted ketone or imine derivatives are efficient methods for accessing chiral alcohols or amines bearing up to three stereogenic centers through a dynamic kinetic resolution (DKR) process. This review provides a summary of recent work in this field, focusing on the development of new catalytic systems and on the extension of these asymmetric reductions to new classes of substrates.
1 Introduction
2 Asymmetric Hydrogenation via Dynamic Kinetic Resolution
2.1 α-Substituted Ketones
2.2. α-Substituted β-Keto Esters and Amides
2.3 α-Substituted β-Keto Phosphonates and Sulfones
2.4 α,α′-Disubstituted Cyclic Ketones
2.5 α,β-Disubstituted Cyclic Ketones
2.6 Imine Derivatives
3 Asymmetric Transfer Hydrogenation via Dynamic Kinetic Resolution
3.1 α-Substituted β-Diketones and Ketones
3.2 α-Substituted β-Keto Esters, Amides and Phosphonates
3.3 β-Substituted α-Keto Esters and Phosphonates
3.4 β-Substituted γ-Keto Esters
3.5 β-Alkoxy Ketones
3.6 Imine Derivatives
4 Conclusion |
doi_str_mv | 10.1055/s-0035-1561648 |
format | Article |
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The transition-metal-catalyzed asymmetric transfer hydrogenation (ATH) and asymmetric hydrogenation (AH) of α- and β-substituted ketone or imine derivatives are efficient methods for accessing chiral alcohols or amines bearing up to three stereogenic centers through a dynamic kinetic resolution (DKR) process. This review provides a summary of recent work in this field, focusing on the development of new catalytic systems and on the extension of these asymmetric reductions to new classes of substrates.
1 Introduction
2 Asymmetric Hydrogenation via Dynamic Kinetic Resolution
2.1 α-Substituted Ketones
2.2. α-Substituted β-Keto Esters and Amides
2.3 α-Substituted β-Keto Phosphonates and Sulfones
2.4 α,α′-Disubstituted Cyclic Ketones
2.5 α,β-Disubstituted Cyclic Ketones
2.6 Imine Derivatives
3 Asymmetric Transfer Hydrogenation via Dynamic Kinetic Resolution
3.1 α-Substituted β-Diketones and Ketones
3.2 α-Substituted β-Keto Esters, Amides and Phosphonates
3.3 β-Substituted α-Keto Esters and Phosphonates
3.4 β-Substituted γ-Keto Esters
3.5 β-Alkoxy Ketones
3.6 Imine Derivatives
4 Conclusion</description><identifier>ISSN: 0039-7881</identifier><identifier>EISSN: 1437-210X</identifier><identifier>DOI: 10.1055/s-0035-1561648</identifier><language>eng</language><publisher>Stuttgart · New York: Georg Thieme Verlag</publisher><subject>short review</subject><ispartof>Synthesis (Stuttgart), 2016-08, Vol.48 (16), p.2523-2539</ispartof><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c317t-2fe30f3d4328e5334d296c10695e3e8277a476f12684face907f997fd68a9a053</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0035-1561648.pdf$$EPDF$$P50$$Gthieme$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.thieme-connect.de/products/ejournals/html/10.1055/s-0035-1561648$$EHTML$$P50$$Gthieme$$Hfree_for_read</linktohtml><link.rule.ids>314,776,780,3004,3005,27901,27902,54534,54535</link.rule.ids></links><search><creatorcontrib>Echeverria, Pierre-Georges</creatorcontrib><creatorcontrib>Ayad, Tahar</creatorcontrib><creatorcontrib>Phansavath, Phannarath</creatorcontrib><creatorcontrib>Ratovelomanana-Vidal, Virginie</creatorcontrib><title>Recent Developments in Asymmetric Hydrogenation and Transfer Hydrogenation of Ketones and Imines through Dynamic Kinetic Resolution</title><title>Synthesis (Stuttgart)</title><addtitle>Synthesis</addtitle><description>Abstract
The transition-metal-catalyzed asymmetric transfer hydrogenation (ATH) and asymmetric hydrogenation (AH) of α- and β-substituted ketone or imine derivatives are efficient methods for accessing chiral alcohols or amines bearing up to three stereogenic centers through a dynamic kinetic resolution (DKR) process. This review provides a summary of recent work in this field, focusing on the development of new catalytic systems and on the extension of these asymmetric reductions to new classes of substrates.
1 Introduction
2 Asymmetric Hydrogenation via Dynamic Kinetic Resolution
2.1 α-Substituted Ketones
2.2. α-Substituted β-Keto Esters and Amides
2.3 α-Substituted β-Keto Phosphonates and Sulfones
2.4 α,α′-Disubstituted Cyclic Ketones
2.5 α,β-Disubstituted Cyclic Ketones
2.6 Imine Derivatives
3 Asymmetric Transfer Hydrogenation via Dynamic Kinetic Resolution
3.1 α-Substituted β-Diketones and Ketones
3.2 α-Substituted β-Keto Esters, Amides and Phosphonates
3.3 β-Substituted α-Keto Esters and Phosphonates
3.4 β-Substituted γ-Keto Esters
3.5 β-Alkoxy Ketones
3.6 Imine Derivatives
4 Conclusion</description><subject>short review</subject><issn>0039-7881</issn><issn>1437-210X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><sourceid>0U6</sourceid><recordid>eNp1UMtKAzEUDaJgrW5d5wdS85iZTJalVVtaEEoFd0OYuWmndJKSpMKs_XEz1pXg6hzueXA5CD0yOmE0z58CoVTkhOUFK7LyCo1YJiThjH5co1GSFJFlyW7RXQgHSqnkQo3Q1wZqsBHP4ROO7tQlHnBr8TT0XQfRtzVe9I13O7A6ts5ibRu89doGA_6P5AxeQXQWwo9r2bUDjXvvzrs9nvdWd6lula4x4QaCO56H4D26MfoY4OEXx-j95Xk7W5D12-tyNl2TWjAZCTcgqBFNJngJuRBZw1VRM1qoHASUXEqdycIwXpSZ0TUoKo1S0jRFqZWmuRijyaW39i4ED6Y6-bbTvq8YrYYJq1ANE1a_E6YAuQTivoUOqoM7e5s-_M__DYtXdLM</recordid><startdate>20160816</startdate><enddate>20160816</enddate><creator>Echeverria, Pierre-Georges</creator><creator>Ayad, Tahar</creator><creator>Phansavath, Phannarath</creator><creator>Ratovelomanana-Vidal, Virginie</creator><general>Georg Thieme Verlag</general><scope>0U6</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20160816</creationdate><title>Recent Developments in Asymmetric Hydrogenation and Transfer Hydrogenation of Ketones and Imines through Dynamic Kinetic Resolution</title><author>Echeverria, Pierre-Georges ; Ayad, Tahar ; Phansavath, Phannarath ; Ratovelomanana-Vidal, Virginie</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c317t-2fe30f3d4328e5334d296c10695e3e8277a476f12684face907f997fd68a9a053</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>short review</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Echeverria, Pierre-Georges</creatorcontrib><creatorcontrib>Ayad, Tahar</creatorcontrib><creatorcontrib>Phansavath, Phannarath</creatorcontrib><creatorcontrib>Ratovelomanana-Vidal, Virginie</creatorcontrib><collection>Thieme Connect Journals Open Access</collection><collection>CrossRef</collection><jtitle>Synthesis (Stuttgart)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Echeverria, Pierre-Georges</au><au>Ayad, Tahar</au><au>Phansavath, Phannarath</au><au>Ratovelomanana-Vidal, Virginie</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Recent Developments in Asymmetric Hydrogenation and Transfer Hydrogenation of Ketones and Imines through Dynamic Kinetic Resolution</atitle><jtitle>Synthesis (Stuttgart)</jtitle><addtitle>Synthesis</addtitle><date>2016-08-16</date><risdate>2016</risdate><volume>48</volume><issue>16</issue><spage>2523</spage><epage>2539</epage><pages>2523-2539</pages><issn>0039-7881</issn><eissn>1437-210X</eissn><abstract>Abstract
The transition-metal-catalyzed asymmetric transfer hydrogenation (ATH) and asymmetric hydrogenation (AH) of α- and β-substituted ketone or imine derivatives are efficient methods for accessing chiral alcohols or amines bearing up to three stereogenic centers through a dynamic kinetic resolution (DKR) process. This review provides a summary of recent work in this field, focusing on the development of new catalytic systems and on the extension of these asymmetric reductions to new classes of substrates.
1 Introduction
2 Asymmetric Hydrogenation via Dynamic Kinetic Resolution
2.1 α-Substituted Ketones
2.2. α-Substituted β-Keto Esters and Amides
2.3 α-Substituted β-Keto Phosphonates and Sulfones
2.4 α,α′-Disubstituted Cyclic Ketones
2.5 α,β-Disubstituted Cyclic Ketones
2.6 Imine Derivatives
3 Asymmetric Transfer Hydrogenation via Dynamic Kinetic Resolution
3.1 α-Substituted β-Diketones and Ketones
3.2 α-Substituted β-Keto Esters, Amides and Phosphonates
3.3 β-Substituted α-Keto Esters and Phosphonates
3.4 β-Substituted γ-Keto Esters
3.5 β-Alkoxy Ketones
3.6 Imine Derivatives
4 Conclusion</abstract><cop>Stuttgart · New York</cop><pub>Georg Thieme Verlag</pub><doi>10.1055/s-0035-1561648</doi><tpages>17</tpages><oa>free_for_read</oa></addata></record> |
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language | eng |
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source | Thieme Connect Journals |
subjects | short review |
title | Recent Developments in Asymmetric Hydrogenation and Transfer Hydrogenation of Ketones and Imines through Dynamic Kinetic Resolution |
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