Synthesis of Chiral 2-Aroyl-1-tetralols: Asymmetric Transfer Hydrgenation of 2-Aroyl-1-tetralones via Dynamic Kinetic Resolution

The dynamic kinetic resolution of 2‐aroyl‐1‐tetralones was achieved via asymmetric transfer hydrogenation using (S,S)‐RuCl(p‐cymene)TsDPEN (TsDPEN=N‐(tosyl)‐1,2‐diphenylethylenediamine) in formic acid/triethyl‐ amine (5:2, molar ratio), afforded the desired products in good yields (up to 85%) with d...

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Published in:Chinese journal of chemistry 2011-07, Vol.29 (7), p.1467-1472
Main Authors: Wu, Yun, Geng, Zhicong, Bai, Jinjin, Zhang, Yawen
Format: Article
Language:English
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2-aroyl-1-tetralones
asymmetric transfer hydrogenation
chiral
Crystal structure
dynamic kinetic resolution
enantioselectivity
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creator Wu, Yun
Geng, Zhicong
Bai, Jinjin
Zhang, Yawen
description The dynamic kinetic resolution of 2‐aroyl‐1‐tetralones was achieved via asymmetric transfer hydrogenation using (S,S)‐RuCl(p‐cymene)TsDPEN (TsDPEN=N‐(tosyl)‐1,2‐diphenylethylenediamine) in formic acid/triethyl‐ amine (5:2, molar ratio), afforded the desired products in good yields (up to 85%) with diastereomeric ratio up to >99:1 and high enantiomeric excesses (up to >99%). The absolute configuration of major the product was confirmed by X‐ray crystal structure analysis. The dynamic kinetic resolution of 2‐aroyl‐1‐tetralones was achieved via asymmetric transfer hydrogenation using (S,S)‐RuCl(p‐cymene)TsDPEN (TsDPEN=N‐(tosyl)‐ 1,2‐diphenylethylenediamine) in formic acid/triethylamine (5:2), affording the desired products in good yields (up to 85%) with diastereomeric ratio up to >99:1 and high enantiomeric excesses (up to >99%). The absolute configuration of major product was confirmed by X‐ray crystal structure analysis.
doi_str_mv 10.1002/cjoc.201180267
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The absolute configuration of major the product was confirmed by X‐ray crystal structure analysis. The dynamic kinetic resolution of 2‐aroyl‐1‐tetralones was achieved via asymmetric transfer hydrogenation using (S,S)‐RuCl(p‐cymene)TsDPEN (TsDPEN=N‐(tosyl)‐ 1,2‐diphenylethylenediamine) in formic acid/triethylamine (5:2), affording the desired products in good yields (up to 85%) with diastereomeric ratio up to &gt;99:1 and high enantiomeric excesses (up to &gt;99%). 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The absolute configuration of major product was confirmed by X‐ray crystal structure analysis.</description><subject>2-aroyl-1-tetralones</subject><subject>asymmetric transfer hydrogenation</subject><subject>chiral</subject><subject>Crystal structure</subject><subject>dynamic kinetic resolution</subject><subject>enantioselectivity</subject><issn>1001-604X</issn><issn>1614-7065</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><recordid>eNqFkDtPwzAUhSMEEqWwMkdidrGdxA-2KqUtD1GpPDfLSRzqksZgp0A2fjqOiiokBqb7Ot-50gmCYwQHCEJ8mi9NPsAQIQYxoTtBDxEUAwpJsut7CBEgMH7aDw6cW3o9pZj0gq_btm4WymkXmjJMF9rKKsRgaE1bAQQa1fiFqdxZOHTtauVHnYd3VtauVDactoV9VrVstKk7_g9YKxe-axmO2lquPHmla9X4OlfOVOsOOwz2Slk5dfRT-8H9-PwunYLr2eQiHV6DPOIJBVmWyQjFjGUqp4RLjJksKIOUsIRTWcICZ3FRFoxwWMYkiniGVVYqjimnLGFRPzjZ-L5a87ZWrhFLs7a1fykQJcQ78STyqsFGlVvjnFWleLV6JW0rEBRdyqJLWWxT9gDfAB-6Uu0_apFeztLfLNiw2jXqc8tK-yL8lSbi8WYi5g_8Jh4nIxFF33svkP0</recordid><startdate>201107</startdate><enddate>201107</enddate><creator>Wu, Yun</creator><creator>Geng, Zhicong</creator><creator>Bai, Jinjin</creator><creator>Zhang, Yawen</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>201107</creationdate><title>Synthesis of Chiral 2-Aroyl-1-tetralols: Asymmetric Transfer Hydrgenation of 2-Aroyl-1-tetralones via Dynamic Kinetic Resolution</title><author>Wu, Yun ; Geng, Zhicong ; Bai, Jinjin ; Zhang, Yawen</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3957-bbba31488bec769a228ad780768597af0d2b4dfd8690f46339b2ebfe927978583</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>2-aroyl-1-tetralones</topic><topic>asymmetric transfer hydrogenation</topic><topic>chiral</topic><topic>Crystal structure</topic><topic>dynamic kinetic resolution</topic><topic>enantioselectivity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wu, Yun</creatorcontrib><creatorcontrib>Geng, Zhicong</creatorcontrib><creatorcontrib>Bai, Jinjin</creatorcontrib><creatorcontrib>Zhang, Yawen</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><jtitle>Chinese journal of chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wu, Yun</au><au>Geng, Zhicong</au><au>Bai, Jinjin</au><au>Zhang, Yawen</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of Chiral 2-Aroyl-1-tetralols: Asymmetric Transfer Hydrgenation of 2-Aroyl-1-tetralones via Dynamic Kinetic Resolution</atitle><jtitle>Chinese journal of chemistry</jtitle><addtitle>Chin. J. Chem</addtitle><date>2011-07</date><risdate>2011</risdate><volume>29</volume><issue>7</issue><spage>1467</spage><epage>1472</epage><pages>1467-1472</pages><issn>1001-604X</issn><eissn>1614-7065</eissn><abstract>The dynamic kinetic resolution of 2‐aroyl‐1‐tetralones was achieved via asymmetric transfer hydrogenation using (S,S)‐RuCl(p‐cymene)TsDPEN (TsDPEN=N‐(tosyl)‐1,2‐diphenylethylenediamine) in formic acid/triethyl‐ amine (5:2, molar ratio), afforded the desired products in good yields (up to 85%) with diastereomeric ratio up to &gt;99:1 and high enantiomeric excesses (up to &gt;99%). The absolute configuration of major the product was confirmed by X‐ray crystal structure analysis. The dynamic kinetic resolution of 2‐aroyl‐1‐tetralones was achieved via asymmetric transfer hydrogenation using (S,S)‐RuCl(p‐cymene)TsDPEN (TsDPEN=N‐(tosyl)‐ 1,2‐diphenylethylenediamine) in formic acid/triethylamine (5:2), affording the desired products in good yields (up to 85%) with diastereomeric ratio up to &gt;99:1 and high enantiomeric excesses (up to &gt;99%). The absolute configuration of major product was confirmed by X‐ray crystal structure analysis.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/cjoc.201180267</doi><tpages>6</tpages><oa>free_for_read</oa></addata></record>
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subjects 2-aroyl-1-tetralones
asymmetric transfer hydrogenation
chiral
Crystal structure
dynamic kinetic resolution
enantioselectivity
title Synthesis of Chiral 2-Aroyl-1-tetralols: Asymmetric Transfer Hydrgenation of 2-Aroyl-1-tetralones via Dynamic Kinetic Resolution
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