Asymmetric Michael Reaction of Acetaldehyde Catalyzed by Diphenylprolinol Silyl Ether
An acetaldehyde breakthrough: The catalytic asymmetric Michael addition reaction of acetaldehyde and various nitroalkenes in the presence of a chiral diphenylprolinol silyl ether organocatalyst is described (see scheme; TMS=trimethylsilyl). The desired 1,4‐addition products, α‐unsubstituted γ‐nitro...
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| Veröffentlicht in: | Angewandte Chemie (International ed.) 2008-06, Vol.47 (25), p.4722-4724 |
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| container_issue | 25 |
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| container_title | Angewandte Chemie (International ed.) |
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| creator | Hayashi, Yujiro Itoh, Takahiko Ohkubo, Masahiro Ishikawa, Hayato |
| description | An acetaldehyde breakthrough: The catalytic asymmetric Michael addition reaction of acetaldehyde and various nitroalkenes in the presence of a chiral diphenylprolinol silyl ether organocatalyst is described (see scheme; TMS=trimethylsilyl). The desired 1,4‐addition products, α‐unsubstituted γ‐nitro aldehydes, were obtained in good yields with excellent enantioselectivities. |
| doi_str_mv | 10.1002/anie.200801130 |
| format | Article |
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The desired 1,4‐addition products, α‐unsubstituted γ‐nitro aldehydes, were obtained in good yields with excellent enantioselectivities.</description><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.200801130</identifier><identifier>PMID: 18435523</identifier><language>eng</language><publisher>Weinheim: Wiley-VCH Verlag</publisher><subject>acetaldehyde ; Acetaldehyde - chemistry ; asymmetric catalysis ; Catalysis ; Ethers - chemistry ; Michael addition ; Molecular Structure ; Proline - analogs & derivatives ; Proline - chemistry ; Solvents - chemistry ; Stereoisomerism ; Styrenes - chemistry ; synthetic methods</subject><ispartof>Angewandte Chemie (International ed.), 2008-06, Vol.47 (25), p.4722-4724</ispartof><rights>Copyright © 2008 WILEY‐VCH Verlag GmbH & Co. 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The desired 1,4‐addition products, α‐unsubstituted γ‐nitro aldehydes, were obtained in good yields with excellent enantioselectivities.</description><subject>acetaldehyde</subject><subject>Acetaldehyde - chemistry</subject><subject>asymmetric catalysis</subject><subject>Catalysis</subject><subject>Ethers - chemistry</subject><subject>Michael addition</subject><subject>Molecular Structure</subject><subject>Proline - analogs & derivatives</subject><subject>Proline - chemistry</subject><subject>Solvents - chemistry</subject><subject>Stereoisomerism</subject><subject>Styrenes - chemistry</subject><subject>synthetic methods</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkE1v1DAURS0Eoh-wZQlZscvgF8d2shxmhlKpFKllhNSNZTsvjMFJBjsjGn49rjIq7Fi9uzj36OkS8groAigt3une4aKgtKIAjD4hp8ALyJmU7GnKJWO5rDickLMYvye-qqh4Tk6gKhnnBTsl22Wcug7H4Gz2ydmdRp_doLajG_psaLOlxVH7BndTg9lKpzz9xiYzU7Z2-x32k9-Hwbt-8Nmt85PPNuMOwwvyrNU-4svjPSfbD5svq4_51eeLy9XyKrelBJpzYQBAozTcyhaqFrCokAtaSq11qY1uDK9txZFraE1trGg5p0UtSisaY9g5eTt70xM_DxhH1blo0Xvd43CISoLgJZM8gYsZtGGIMWCr9sF1OkwKqHoYUj0MqR6HTIXXR_PBdNj8xY_LJaCegV_O4_QfnVpeX27-ledz18UR7x-7OvxQQqZ31dfrCyWLm_Xd3fu1gsS_mflWD0p_Cy6q7W1Bk4rWVJQC2B-UKZiz</recordid><startdate>20080609</startdate><enddate>20080609</enddate><creator>Hayashi, Yujiro</creator><creator>Itoh, Takahiko</creator><creator>Ohkubo, Masahiro</creator><creator>Ishikawa, Hayato</creator><general>Wiley-VCH Verlag</general><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>FBQ</scope><scope>BSCLL</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20080609</creationdate><title>Asymmetric Michael Reaction of Acetaldehyde Catalyzed by Diphenylprolinol Silyl Ether</title><author>Hayashi, Yujiro ; Itoh, Takahiko ; Ohkubo, Masahiro ; Ishikawa, Hayato</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4710-56b111ae7b5c7f18f1e28e56047aaa4abadb59c85e5a1fb9bc6f5502964c6dbb3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><topic>acetaldehyde</topic><topic>Acetaldehyde - chemistry</topic><topic>asymmetric catalysis</topic><topic>Catalysis</topic><topic>Ethers - chemistry</topic><topic>Michael addition</topic><topic>Molecular Structure</topic><topic>Proline - analogs & derivatives</topic><topic>Proline - chemistry</topic><topic>Solvents - chemistry</topic><topic>Stereoisomerism</topic><topic>Styrenes - chemistry</topic><topic>synthetic methods</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hayashi, Yujiro</creatorcontrib><creatorcontrib>Itoh, Takahiko</creatorcontrib><creatorcontrib>Ohkubo, Masahiro</creatorcontrib><creatorcontrib>Ishikawa, Hayato</creatorcontrib><collection>AGRIS</collection><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Angewandte Chemie (International ed.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hayashi, Yujiro</au><au>Itoh, Takahiko</au><au>Ohkubo, Masahiro</au><au>Ishikawa, Hayato</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Asymmetric Michael Reaction of Acetaldehyde Catalyzed by Diphenylprolinol Silyl Ether</atitle><jtitle>Angewandte Chemie (International ed.)</jtitle><addtitle>Angewandte Chemie International Edition</addtitle><date>2008-06-09</date><risdate>2008</risdate><volume>47</volume><issue>25</issue><spage>4722</spage><epage>4724</epage><pages>4722-4724</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>An acetaldehyde breakthrough: The catalytic asymmetric Michael addition reaction of acetaldehyde and various nitroalkenes in the presence of a chiral diphenylprolinol silyl ether organocatalyst is described (see scheme; TMS=trimethylsilyl). The desired 1,4‐addition products, α‐unsubstituted γ‐nitro aldehydes, were obtained in good yields with excellent enantioselectivities.</abstract><cop>Weinheim</cop><pub>Wiley-VCH Verlag</pub><pmid>18435523</pmid><doi>10.1002/anie.200801130</doi><tpages>3</tpages></addata></record> |
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| ispartof | Angewandte Chemie (International ed.), 2008-06, Vol.47 (25), p.4722-4724 |
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| language | eng |
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| source | MEDLINE; Wiley Online Library Journals Frontfile Complete |
| subjects | acetaldehyde Acetaldehyde - chemistry asymmetric catalysis Catalysis Ethers - chemistry Michael addition Molecular Structure Proline - analogs & derivatives Proline - chemistry Solvents - chemistry Stereoisomerism Styrenes - chemistry synthetic methods |
| title | Asymmetric Michael Reaction of Acetaldehyde Catalyzed by Diphenylprolinol Silyl Ether |
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