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Highly Enantioselective Aza-Baylis-Hillman-Type Reaction of α,β-Unsaturated Aldehydes with In Situ Generated N-Boc- and N-Cbz-Imines
An organocatalytic highly enantioselective aza‐Baylis–Hillman reaction of α,β‐unsaturated aldehydes with in situ generated N‐Boc‐ and N‐Cbz‐imines is presented. This novel process opens the pathway for the synthesis of β‐amino carbonyl compounds bearing an α‐alkylidene group under mild and simple co...
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| Published in: | European Journal of Organic Chemistry 2009-12, Vol.2009 (36), p.6277-6280 |
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| Main Authors: | , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c3579-2d8126c5810d489d6d145977a7ca51811eef6a14897e0c3e95d915d7422108ff3 |
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| cites | cdi_FETCH-LOGICAL-c3579-2d8126c5810d489d6d145977a7ca51811eef6a14897e0c3e95d915d7422108ff3 |
| container_end_page | 6280 |
| container_issue | 36 |
| container_start_page | 6277 |
| container_title | European Journal of Organic Chemistry |
| container_volume | 2009 |
| creator | CIHALOVA, Sylva REMES, Marek CISAROVA, Ivana VESELY, Jan |
| description | An organocatalytic highly enantioselective aza‐Baylis–Hillman reaction of α,β‐unsaturated aldehydes with in situ generated N‐Boc‐ and N‐Cbz‐imines is presented. This novel process opens the pathway for the synthesis of β‐amino carbonyl compounds bearing an α‐alkylidene group under mild and simple conditions. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
Chiral β‐amino carbonyl compounds bearing an α‐alkylidene group were easily synthesized under mild and simple conditions from α,β‐unsaturated aldehydes and α‐amido sulfones in good yields and diastereoselectivities and excellent enantioselectivities. |
| doi_str_mv | 10.1002/ejoc.200900969 |
| format | article |
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Chiral β‐amino carbonyl compounds bearing an α‐alkylidene group were easily synthesized under mild and simple conditions from α,β‐unsaturated aldehydes and α‐amido sulfones in good yields and diastereoselectivities and excellent enantioselectivities.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.200900969</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Aza-Baylis-Hillman reaction ; Catalysis ; Catalytic reactions ; Chemistry ; Diastereoselectivity ; Enantioselectivity ; Exact sciences and technology ; General and physical chemistry ; Noncondensed benzenic compounds ; Organic chemistry ; Organocatalysis ; Preparations and properties ; Sulfur ; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry</subject><ispartof>European Journal of Organic Chemistry, 2009-12, Vol.2009 (36), p.6277-6280</ispartof><rights>Copyright © 2009 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3579-2d8126c5810d489d6d145977a7ca51811eef6a14897e0c3e95d915d7422108ff3</citedby><cites>FETCH-LOGICAL-c3579-2d8126c5810d489d6d145977a7ca51811eef6a14897e0c3e95d915d7422108ff3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>313,314,780,784,792,27920,27922,27923</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=22229247$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>CIHALOVA, Sylva</creatorcontrib><creatorcontrib>REMES, Marek</creatorcontrib><creatorcontrib>CISAROVA, Ivana</creatorcontrib><creatorcontrib>VESELY, Jan</creatorcontrib><title>Highly Enantioselective Aza-Baylis-Hillman-Type Reaction of α,β-Unsaturated Aldehydes with In Situ Generated N-Boc- and N-Cbz-Imines</title><title>European Journal of Organic Chemistry</title><addtitle>Eur. J. Org. Chem</addtitle><description>An organocatalytic highly enantioselective aza‐Baylis–Hillman reaction of α,β‐unsaturated aldehydes with in situ generated N‐Boc‐ and N‐Cbz‐imines is presented. This novel process opens the pathway for the synthesis of β‐amino carbonyl compounds bearing an α‐alkylidene group under mild and simple conditions. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
Chiral β‐amino carbonyl compounds bearing an α‐alkylidene group were easily synthesized under mild and simple conditions from α,β‐unsaturated aldehydes and α‐amido sulfones in good yields and diastereoselectivities and excellent enantioselectivities.</description><subject>Aza-Baylis-Hillman reaction</subject><subject>Catalysis</subject><subject>Catalytic reactions</subject><subject>Chemistry</subject><subject>Diastereoselectivity</subject><subject>Enantioselectivity</subject><subject>Exact sciences and technology</subject><subject>General and physical chemistry</subject><subject>Noncondensed benzenic compounds</subject><subject>Organic chemistry</subject><subject>Organocatalysis</subject><subject>Preparations and properties</subject><subject>Sulfur</subject><subject>Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><recordid>eNqFkM1OGzEQx1eISnyUK2dfesOp7f3w-hhCSNIiUPkQ3KypPUtMHW-0XkqXB-j7tA_CM3WjraLeao3kkeb3m5H-SXLM2YgzJj7iU21GgjHVV6F2kn3OlKKsUGy377M0o1ylD3vJQYxPbMMUfD_5OXePS9-RaYDQujqiR9O670jGr0BPofMu0rnzfgWB3nZrJNcIPVAHUlfk7dfJ2296FyK0zw20aMnYW1x2FiN5ce2SLAK5ce0zmWHAAbikp7WhBMKmnXx9pYuVCxjfJ-8q8BGP_v6Hyd359HYypxdXs8VkfEFNmktFhS25KExecmazUtnC8ixXUoI0kPOSc8SqAN6PJDKTosqt4rmVmRCclVWVHiajYa9p6hgbrPS6cStoOs2Z3qSoNynqbYq98GEQ1hAN-KqBYFzcWqJ_SmSy59TAvTiP3X-26umnq8m_N-jgutjij60LzTddyFTm-v5ypsXZ5-KsnH3R5-kfDH6T2Q</recordid><startdate>200912</startdate><enddate>200912</enddate><creator>CIHALOVA, Sylva</creator><creator>REMES, Marek</creator><creator>CISAROVA, Ivana</creator><creator>VESELY, Jan</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley-VCH</general><scope>BSCLL</scope><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>200912</creationdate><title>Highly Enantioselective Aza-Baylis-Hillman-Type Reaction of α,β-Unsaturated Aldehydes with In Situ Generated N-Boc- and N-Cbz-Imines</title><author>CIHALOVA, Sylva ; REMES, Marek ; CISAROVA, Ivana ; VESELY, Jan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3579-2d8126c5810d489d6d145977a7ca51811eef6a14897e0c3e95d915d7422108ff3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>Aza-Baylis-Hillman reaction</topic><topic>Catalysis</topic><topic>Catalytic reactions</topic><topic>Chemistry</topic><topic>Diastereoselectivity</topic><topic>Enantioselectivity</topic><topic>Exact sciences and technology</topic><topic>General and physical chemistry</topic><topic>Noncondensed benzenic compounds</topic><topic>Organic chemistry</topic><topic>Organocatalysis</topic><topic>Preparations and properties</topic><topic>Sulfur</topic><topic>Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>CIHALOVA, Sylva</creatorcontrib><creatorcontrib>REMES, Marek</creatorcontrib><creatorcontrib>CISAROVA, Ivana</creatorcontrib><creatorcontrib>VESELY, Jan</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>CrossRef</collection><jtitle>European Journal of Organic Chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>CIHALOVA, Sylva</au><au>REMES, Marek</au><au>CISAROVA, Ivana</au><au>VESELY, Jan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Highly Enantioselective Aza-Baylis-Hillman-Type Reaction of α,β-Unsaturated Aldehydes with In Situ Generated N-Boc- and N-Cbz-Imines</atitle><jtitle>European Journal of Organic Chemistry</jtitle><addtitle>Eur. J. Org. Chem</addtitle><date>2009-12</date><risdate>2009</risdate><volume>2009</volume><issue>36</issue><spage>6277</spage><epage>6280</epage><pages>6277-6280</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>An organocatalytic highly enantioselective aza‐Baylis–Hillman reaction of α,β‐unsaturated aldehydes with in situ generated N‐Boc‐ and N‐Cbz‐imines is presented. This novel process opens the pathway for the synthesis of β‐amino carbonyl compounds bearing an α‐alkylidene group under mild and simple conditions. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
Chiral β‐amino carbonyl compounds bearing an α‐alkylidene group were easily synthesized under mild and simple conditions from α,β‐unsaturated aldehydes and α‐amido sulfones in good yields and diastereoselectivities and excellent enantioselectivities.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/ejoc.200900969</doi><tpages>4</tpages></addata></record> |
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| identifier | ISSN: 1434-193X |
| ispartof | European Journal of Organic Chemistry, 2009-12, Vol.2009 (36), p.6277-6280 |
| issn | 1434-193X 1099-0690 |
| language | eng |
| recordid | cdi_crossref_primary_10_1002_ejoc_200900969 |
| source | Wiley-Blackwell Read & Publish Collection |
| subjects | Aza-Baylis-Hillman reaction Catalysis Catalytic reactions Chemistry Diastereoselectivity Enantioselectivity Exact sciences and technology General and physical chemistry Noncondensed benzenic compounds Organic chemistry Organocatalysis Preparations and properties Sulfur Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry |
| title | Highly Enantioselective Aza-Baylis-Hillman-Type Reaction of α,β-Unsaturated Aldehydes with In Situ Generated N-Boc- and N-Cbz-Imines |
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