7-Azaindoline Auxiliary: A Versatile Attachment Facilitating Enantioselective C–C Bond-Forming Catalysis
Abstract This short review provides an overview of 7-azaindoline auxiliaries in asymmetric catalysis. 7-Azaindoline serves as a useful attachment to carboxylic acids, and the thus-formed 7-azaindoline amides are amenable to atom-economical C–C bond-forming reactions with high stereoselectivity. The...
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| Veröffentlicht in: | Synthesis (Stuttgart) 2019-01, Vol.51 (1), p.185-193 |
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| container_title | Synthesis (Stuttgart) |
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| creator | Kumagai, Naoya Shibasaki, Masakatsu |
| description | Abstract
This short review provides an overview of 7-azaindoline auxiliaries in asymmetric catalysis. 7-Azaindoline serves as a useful attachment to carboxylic acids, and the thus-formed 7-azaindoline amides are amenable to atom-economical C–C bond-forming reactions with high stereoselectivity. The attachment is used for the sake of gaining traction in promoting the reaction of interest and can be easily removed after enantioselective reactions. Both nucleophilic and electrophilic catalyses are realized with broad tolerance for functional groups, showcasing the usefulness of 7-azaindoline auxiliaries for practical and streamlined synthesis of a wide range of acyclic chiral building blocks.
1 Introduction
2 7-Azaindoline as a Key Auxiliary
3 7-Azaindoline Amide as a Pronucleophile
3.1 α-Carbon-Substituted 7-Azaindoline Amide
3.2 α-Nitrogen-Substituted 7-Azaindoline Amide
3.3 α-Oxygen-Substituted 7-Azaindoline Amide
3.4 α-Fluorocarbon-Substituted 7-Azaindoline Amide
3.5 α-Halogen-Substituted 7-Azaindoline Amide
3.6 α-Sulfur-Substituted 7-Azaindoline Amide
4 7-Azaindoline Amide as an Electrophile
4.1 Conjugate Addition of Butenolides
4.2 1,3-Dipolar Cycloaddition of Nitrones
5 Transformation of 7-Azaindoline Amide
6 Conclusion |
| doi_str_mv | 10.1055/s-0037-1610412 |
| format | Article |
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This short review provides an overview of 7-azaindoline auxiliaries in asymmetric catalysis. 7-Azaindoline serves as a useful attachment to carboxylic acids, and the thus-formed 7-azaindoline amides are amenable to atom-economical C–C bond-forming reactions with high stereoselectivity. The attachment is used for the sake of gaining traction in promoting the reaction of interest and can be easily removed after enantioselective reactions. Both nucleophilic and electrophilic catalyses are realized with broad tolerance for functional groups, showcasing the usefulness of 7-azaindoline auxiliaries for practical and streamlined synthesis of a wide range of acyclic chiral building blocks.
1 Introduction
2 7-Azaindoline as a Key Auxiliary
3 7-Azaindoline Amide as a Pronucleophile
3.1 α-Carbon-Substituted 7-Azaindoline Amide
3.2 α-Nitrogen-Substituted 7-Azaindoline Amide
3.3 α-Oxygen-Substituted 7-Azaindoline Amide
3.4 α-Fluorocarbon-Substituted 7-Azaindoline Amide
3.5 α-Halogen-Substituted 7-Azaindoline Amide
3.6 α-Sulfur-Substituted 7-Azaindoline Amide
4 7-Azaindoline Amide as an Electrophile
4.1 Conjugate Addition of Butenolides
4.2 1,3-Dipolar Cycloaddition of Nitrones
5 Transformation of 7-Azaindoline Amide
6 Conclusion</description><identifier>ISSN: 0039-7881</identifier><identifier>EISSN: 1437-210X</identifier><identifier>DOI: 10.1055/s-0037-1610412</identifier><language>eng</language><publisher>Stuttgart · New York: Georg Thieme Verlag</publisher><subject>short review</subject><ispartof>Synthesis (Stuttgart), 2019-01, Vol.51 (1), p.185-193</ispartof><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c313t-92fe398109239dc418816ce69b6a7291f165fb895ef0caaa170863f19507f7563</citedby><orcidid>0000-0001-8862-582X ; 0000-0003-1843-2592</orcidid></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-0037-1610412.pdf$$EPDF$$P50$$Gthieme$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.thieme-connect.de/products/ejournals/html/10.1055/s-0037-1610412$$EHTML$$P50$$Gthieme$$Hfree_for_read</linktohtml><link.rule.ids>314,780,784,3017,3018,27924,27925,54559,54560</link.rule.ids></links><search><creatorcontrib>Kumagai, Naoya</creatorcontrib><creatorcontrib>Shibasaki, Masakatsu</creatorcontrib><title>7-Azaindoline Auxiliary: A Versatile Attachment Facilitating Enantioselective C–C Bond-Forming Catalysis</title><title>Synthesis (Stuttgart)</title><addtitle>Synthesis</addtitle><description>Abstract
This short review provides an overview of 7-azaindoline auxiliaries in asymmetric catalysis. 7-Azaindoline serves as a useful attachment to carboxylic acids, and the thus-formed 7-azaindoline amides are amenable to atom-economical C–C bond-forming reactions with high stereoselectivity. The attachment is used for the sake of gaining traction in promoting the reaction of interest and can be easily removed after enantioselective reactions. Both nucleophilic and electrophilic catalyses are realized with broad tolerance for functional groups, showcasing the usefulness of 7-azaindoline auxiliaries for practical and streamlined synthesis of a wide range of acyclic chiral building blocks.
1 Introduction
2 7-Azaindoline as a Key Auxiliary
3 7-Azaindoline Amide as a Pronucleophile
3.1 α-Carbon-Substituted 7-Azaindoline Amide
3.2 α-Nitrogen-Substituted 7-Azaindoline Amide
3.3 α-Oxygen-Substituted 7-Azaindoline Amide
3.4 α-Fluorocarbon-Substituted 7-Azaindoline Amide
3.5 α-Halogen-Substituted 7-Azaindoline Amide
3.6 α-Sulfur-Substituted 7-Azaindoline Amide
4 7-Azaindoline Amide as an Electrophile
4.1 Conjugate Addition of Butenolides
4.2 1,3-Dipolar Cycloaddition of Nitrones
5 Transformation of 7-Azaindoline Amide
6 Conclusion</description><subject>short review</subject><issn>0039-7881</issn><issn>1437-210X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><sourceid>0U6</sourceid><recordid>eNp1UEFOwzAQtBBIlMKVsz_g4k0aO-YWorYgVeICiJvlujZ1lTgodhHlxB94B5_gKbwEV-2V02pnZ1Yzg9Al0BHQorgKhNKcE2BAx5AdoQGM05oBfT5Gg3QShJclnKKzENaUUp7lYoAaTqoP5fyya5w3uNq8u8apfnuNK_xk-qCiaxIco9Kr1viIp0onRky4f8ETr3x0XTCN0dG9mZ9vXP9-ftX4pvNLMu36dseqVVTNNrhwjk6saoK5OMwhepxOHupbMr-f3dXVnOgc8khEZk0uSqAiWVzqMSTbTBsmFkzxTIAFVthFKQpjqVZKAaclyy2IgnLLC5YP0Wj_V_ddCL2x8rV3bUolgcpdVzLIXVfy0FUSkL0grpxpjVx3m94nh__x_wC852wz</recordid><startdate>20190101</startdate><enddate>20190101</enddate><creator>Kumagai, Naoya</creator><creator>Shibasaki, Masakatsu</creator><general>Georg Thieme Verlag</general><scope>0U6</scope><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0001-8862-582X</orcidid><orcidid>https://orcid.org/0000-0003-1843-2592</orcidid></search><sort><creationdate>20190101</creationdate><title>7-Azaindoline Auxiliary: A Versatile Attachment Facilitating Enantioselective C–C Bond-Forming Catalysis</title><author>Kumagai, Naoya ; Shibasaki, Masakatsu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c313t-92fe398109239dc418816ce69b6a7291f165fb895ef0caaa170863f19507f7563</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>short review</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kumagai, Naoya</creatorcontrib><creatorcontrib>Shibasaki, Masakatsu</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>Kumagai, Naoya</au><au>Shibasaki, Masakatsu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>7-Azaindoline Auxiliary: A Versatile Attachment Facilitating Enantioselective C–C Bond-Forming Catalysis</atitle><jtitle>Synthesis (Stuttgart)</jtitle><addtitle>Synthesis</addtitle><date>2019-01-01</date><risdate>2019</risdate><volume>51</volume><issue>1</issue><spage>185</spage><epage>193</epage><pages>185-193</pages><issn>0039-7881</issn><eissn>1437-210X</eissn><abstract>Abstract
This short review provides an overview of 7-azaindoline auxiliaries in asymmetric catalysis. 7-Azaindoline serves as a useful attachment to carboxylic acids, and the thus-formed 7-azaindoline amides are amenable to atom-economical C–C bond-forming reactions with high stereoselectivity. The attachment is used for the sake of gaining traction in promoting the reaction of interest and can be easily removed after enantioselective reactions. Both nucleophilic and electrophilic catalyses are realized with broad tolerance for functional groups, showcasing the usefulness of 7-azaindoline auxiliaries for practical and streamlined synthesis of a wide range of acyclic chiral building blocks.
1 Introduction
2 7-Azaindoline as a Key Auxiliary
3 7-Azaindoline Amide as a Pronucleophile
3.1 α-Carbon-Substituted 7-Azaindoline Amide
3.2 α-Nitrogen-Substituted 7-Azaindoline Amide
3.3 α-Oxygen-Substituted 7-Azaindoline Amide
3.4 α-Fluorocarbon-Substituted 7-Azaindoline Amide
3.5 α-Halogen-Substituted 7-Azaindoline Amide
3.6 α-Sulfur-Substituted 7-Azaindoline Amide
4 7-Azaindoline Amide as an Electrophile
4.1 Conjugate Addition of Butenolides
4.2 1,3-Dipolar Cycloaddition of Nitrones
5 Transformation of 7-Azaindoline Amide
6 Conclusion</abstract><cop>Stuttgart · New York</cop><pub>Georg Thieme Verlag</pub><doi>10.1055/s-0037-1610412</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0001-8862-582X</orcidid><orcidid>https://orcid.org/0000-0003-1843-2592</orcidid><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 | 7-Azaindoline Auxiliary: A Versatile Attachment Facilitating Enantioselective C–C Bond-Forming Catalysis |
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