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Amide‐phosphonium Salt Catalyzed Enantioselective Vinylogous Mannich Addition of Coumarins to Isatin Imines
An asymmetric vinylogous Mannich reaction between 3‐cyano‐4‐methylcoumarins and N‐Boc isatin imines catalysed by amide phosphonium salt is described. This method allows the formation of intriguing adducts bearing both 3‐aminooxindole and coumarin moieties in excellent yields with excellent enantiose...
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Published in: | ChemCatChem 2020-01, Vol.12 (2), p.444-448 |
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creator | Wang, Jing Zhang, Shuo Ding, Weizhong Wang, Chenghan Chen, Jie Cao, Weiguo Wu, Xiaoyu |
description | An asymmetric vinylogous Mannich reaction between 3‐cyano‐4‐methylcoumarins and N‐Boc isatin imines catalysed by amide phosphonium salt is described. This method allows the formation of intriguing adducts bearing both 3‐aminooxindole and coumarin moieties in excellent yields with excellent enantioselectivities. The utility of this method was illustrated by a gram scale synthesis using as low as 0.1 mol % of catalyst without chromatographic purification, and removal of the Boc protecting groups on the primary amine functionality in Mannich products.
Phosphine catalysis: Under 0.1 mol % of phosphonium salt catalyst, vinylogous Mannich reaction between 3‐cyano‐4‐methylcoumarins and N‐Boc isatin imines has been developed. This method allows the formation of intriguing adducts bearing both 3‐aminooxindole and coumarin moieties in excellent yields with excellent enantioselectivities. The utility of this method was illustrated by a gram scale synthesis without chromatographic purification, and removal of the Boc protecting groups on the primary amine functionality in Mannich products. |
doi_str_mv | 10.1002/cctc.201901677 |
format | article |
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Phosphine catalysis: Under 0.1 mol % of phosphonium salt catalyst, vinylogous Mannich reaction between 3‐cyano‐4‐methylcoumarins and N‐Boc isatin imines has been developed. This method allows the formation of intriguing adducts bearing both 3‐aminooxindole and coumarin moieties in excellent yields with excellent enantioselectivities. The utility of this method was illustrated by a gram scale synthesis without chromatographic purification, and removal of the Boc protecting groups on the primary amine functionality in Mannich products.</description><identifier>ISSN: 1867-3880</identifier><identifier>EISSN: 1867-3899</identifier><identifier>DOI: 10.1002/cctc.201901677</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Adducts ; Asymmetric ; Coumarin ; Enantiomers ; Imines ; Mannich reaction ; Oxindole ; Vinylogous</subject><ispartof>ChemCatChem, 2020-01, Vol.12 (2), p.444-448</ispartof><rights>2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2020 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3837-96dbb22ca9f3fa3eea296ab142affa92a1cb147769d34ad174771510bcb46ed3</citedby><cites>FETCH-LOGICAL-c3837-96dbb22ca9f3fa3eea296ab142affa92a1cb147769d34ad174771510bcb46ed3</cites><orcidid>0000-0001-7179-4280</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Wang, Jing</creatorcontrib><creatorcontrib>Zhang, Shuo</creatorcontrib><creatorcontrib>Ding, Weizhong</creatorcontrib><creatorcontrib>Wang, Chenghan</creatorcontrib><creatorcontrib>Chen, Jie</creatorcontrib><creatorcontrib>Cao, Weiguo</creatorcontrib><creatorcontrib>Wu, Xiaoyu</creatorcontrib><title>Amide‐phosphonium Salt Catalyzed Enantioselective Vinylogous Mannich Addition of Coumarins to Isatin Imines</title><title>ChemCatChem</title><description>An asymmetric vinylogous Mannich reaction between 3‐cyano‐4‐methylcoumarins and N‐Boc isatin imines catalysed by amide phosphonium salt is described. This method allows the formation of intriguing adducts bearing both 3‐aminooxindole and coumarin moieties in excellent yields with excellent enantioselectivities. The utility of this method was illustrated by a gram scale synthesis using as low as 0.1 mol % of catalyst without chromatographic purification, and removal of the Boc protecting groups on the primary amine functionality in Mannich products.
Phosphine catalysis: Under 0.1 mol % of phosphonium salt catalyst, vinylogous Mannich reaction between 3‐cyano‐4‐methylcoumarins and N‐Boc isatin imines has been developed. This method allows the formation of intriguing adducts bearing both 3‐aminooxindole and coumarin moieties in excellent yields with excellent enantioselectivities. The utility of this method was illustrated by a gram scale synthesis without chromatographic purification, and removal of the Boc protecting groups on the primary amine functionality in Mannich products.</description><subject>Adducts</subject><subject>Asymmetric</subject><subject>Coumarin</subject><subject>Enantiomers</subject><subject>Imines</subject><subject>Mannich reaction</subject><subject>Oxindole</subject><subject>Vinylogous</subject><issn>1867-3880</issn><issn>1867-3899</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNqFkM9KAzEQxoMoWKtXzwHPrfmz3WyOZalaqHiweA3ZJGtTdpO6ySrryUfwGX0SUyp69DDMN_D7ZoYPgEuMphghcq1UVFOCMEc4Z-wIjHCRswktOD_-1QU6BWchbBHKOWWzEWjnrdXm6-Nzt_EhlbN9Cx9lE2Epo2yGd6PhwkkXrQ-mMSraVwOfrBsa_-z7AO-lc1Zt4FxrmxgHfQ1L37eysy7A6OEyyGgdXLbWmXAOTmrZBHPx08dgfbNYl3eT1cPtspyvJooWlE14rquKECV5TWtJjZGE57LCGZF1LTmRWKWBsZxrmkmNWdJ4hlGlqiw3mo7B1WHtrvMvvQlRbH3fuXRREJrRjBBazBI1PVCq8yF0pha7zqbHB4GR2Ccq9omK30STgR8Mb7Yxwz-0KMt1-ef9BsR8fcM</recordid><startdate>20200118</startdate><enddate>20200118</enddate><creator>Wang, Jing</creator><creator>Zhang, Shuo</creator><creator>Ding, Weizhong</creator><creator>Wang, Chenghan</creator><creator>Chen, Jie</creator><creator>Cao, Weiguo</creator><creator>Wu, Xiaoyu</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0001-7179-4280</orcidid></search><sort><creationdate>20200118</creationdate><title>Amide‐phosphonium Salt Catalyzed Enantioselective Vinylogous Mannich Addition of Coumarins to Isatin Imines</title><author>Wang, Jing ; Zhang, Shuo ; Ding, Weizhong ; Wang, Chenghan ; Chen, Jie ; Cao, Weiguo ; Wu, Xiaoyu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3837-96dbb22ca9f3fa3eea296ab142affa92a1cb147769d34ad174771510bcb46ed3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Adducts</topic><topic>Asymmetric</topic><topic>Coumarin</topic><topic>Enantiomers</topic><topic>Imines</topic><topic>Mannich reaction</topic><topic>Oxindole</topic><topic>Vinylogous</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wang, Jing</creatorcontrib><creatorcontrib>Zhang, Shuo</creatorcontrib><creatorcontrib>Ding, Weizhong</creatorcontrib><creatorcontrib>Wang, Chenghan</creatorcontrib><creatorcontrib>Chen, Jie</creatorcontrib><creatorcontrib>Cao, Weiguo</creatorcontrib><creatorcontrib>Wu, Xiaoyu</creatorcontrib><collection>CrossRef</collection><jtitle>ChemCatChem</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wang, Jing</au><au>Zhang, Shuo</au><au>Ding, Weizhong</au><au>Wang, Chenghan</au><au>Chen, Jie</au><au>Cao, Weiguo</au><au>Wu, Xiaoyu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Amide‐phosphonium Salt Catalyzed Enantioselective Vinylogous Mannich Addition of Coumarins to Isatin Imines</atitle><jtitle>ChemCatChem</jtitle><date>2020-01-18</date><risdate>2020</risdate><volume>12</volume><issue>2</issue><spage>444</spage><epage>448</epage><pages>444-448</pages><issn>1867-3880</issn><eissn>1867-3899</eissn><abstract>An asymmetric vinylogous Mannich reaction between 3‐cyano‐4‐methylcoumarins and N‐Boc isatin imines catalysed by amide phosphonium salt is described. This method allows the formation of intriguing adducts bearing both 3‐aminooxindole and coumarin moieties in excellent yields with excellent enantioselectivities. The utility of this method was illustrated by a gram scale synthesis using as low as 0.1 mol % of catalyst without chromatographic purification, and removal of the Boc protecting groups on the primary amine functionality in Mannich products.
Phosphine catalysis: Under 0.1 mol % of phosphonium salt catalyst, vinylogous Mannich reaction between 3‐cyano‐4‐methylcoumarins and N‐Boc isatin imines has been developed. This method allows the formation of intriguing adducts bearing both 3‐aminooxindole and coumarin moieties in excellent yields with excellent enantioselectivities. The utility of this method was illustrated by a gram scale synthesis without chromatographic purification, and removal of the Boc protecting groups on the primary amine functionality in Mannich products.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/cctc.201901677</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0001-7179-4280</orcidid></addata></record> |
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subjects | Adducts Asymmetric Coumarin Enantiomers Imines Mannich reaction Oxindole Vinylogous |
title | Amide‐phosphonium Salt Catalyzed Enantioselective Vinylogous Mannich Addition of Coumarins to Isatin Imines |
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