N -Nosyl- O -bromoethyl hydroxylamine acts as a multifunctional formaldehyde, formaldimine, and 1,2-oxazetidine surrogate for C–C and C–O bond-forming reactions
We describe that N -nosyl- O -bromoethyl hydroxylamine, a bench stable solid, could function as a novel formaldehyde, formaldimine, and 1,2-oxazetidine surrogate under DBU basic conditions. By merely using this simple reagent, a broad range of synthetically useful α-hydroxymethyl and α-aminomethyl k...
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| Veröffentlicht in: | Organic Chemistry Frontiers 2021-09, Vol.8 (18), p.5124-5129 |
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| container_issue | 18 |
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| container_title | Organic Chemistry Frontiers |
| container_volume | 8 |
| creator | Wu, Binyu Wen, Xiaolu Chen, Hongbing Hu, Lin |
| description | We describe that
N
-nosyl-
O
-bromoethyl hydroxylamine, a bench stable solid, could function as a novel formaldehyde, formaldimine, and 1,2-oxazetidine surrogate under DBU basic conditions. By merely using this simple reagent, a broad range of synthetically useful α-hydroxymethyl and α-aminomethyl ketones, as well as chiral α-alkoxyl and α-aminomethyl indanone carboxylates could be divergently obtained
via
chemo- and stereoselective aldol, Mannich or umpolung C–O bond-forming reactions. The challenging catalytic asymmetric Mannich reaction of formaldimine equivalent was also realized with moderate enantioselectivities. |
| doi_str_mv | 10.1039/D1QO00748C |
| format | Article |
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N
-nosyl-
O
-bromoethyl hydroxylamine, a bench stable solid, could function as a novel formaldehyde, formaldimine, and 1,2-oxazetidine surrogate under DBU basic conditions. By merely using this simple reagent, a broad range of synthetically useful α-hydroxymethyl and α-aminomethyl ketones, as well as chiral α-alkoxyl and α-aminomethyl indanone carboxylates could be divergently obtained
via
chemo- and stereoselective aldol, Mannich or umpolung C–O bond-forming reactions. The challenging catalytic asymmetric Mannich reaction of formaldimine equivalent was also realized with moderate enantioselectivities.</description><identifier>ISSN: 2052-4129</identifier><identifier>ISSN: 2052-4110</identifier><identifier>EISSN: 2052-4129</identifier><identifier>EISSN: 2052-4110</identifier><identifier>DOI: 10.1039/D1QO00748C</identifier><language>eng</language><publisher>London: Royal Society of Chemistry</publisher><subject>Aldehydes ; Carboxylates ; Divergence ; Formaldehyde ; Hydroxylamine ; Ketones ; NMR ; Nuclear magnetic resonance ; Optimization ; Organic chemistry ; Reagents ; Stereoselectivity</subject><ispartof>Organic Chemistry Frontiers, 2021-09, Vol.8 (18), p.5124-5129</ispartof><rights>Copyright Royal Society of Chemistry 2021</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c259t-86906649a843d601ef6afd063cd0f9ea830d9bd3360480c8fc7368a1519844223</citedby><cites>FETCH-LOGICAL-c259t-86906649a843d601ef6afd063cd0f9ea830d9bd3360480c8fc7368a1519844223</cites><orcidid>0000-0002-8600-965X</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>Wu, Binyu</creatorcontrib><creatorcontrib>Wen, Xiaolu</creatorcontrib><creatorcontrib>Chen, Hongbing</creatorcontrib><creatorcontrib>Hu, Lin</creatorcontrib><title>N -Nosyl- O -bromoethyl hydroxylamine acts as a multifunctional formaldehyde, formaldimine, and 1,2-oxazetidine surrogate for C–C and C–O bond-forming reactions</title><title>Organic Chemistry Frontiers</title><description>We describe that
N
-nosyl-
O
-bromoethyl hydroxylamine, a bench stable solid, could function as a novel formaldehyde, formaldimine, and 1,2-oxazetidine surrogate under DBU basic conditions. By merely using this simple reagent, a broad range of synthetically useful α-hydroxymethyl and α-aminomethyl ketones, as well as chiral α-alkoxyl and α-aminomethyl indanone carboxylates could be divergently obtained
via
chemo- and stereoselective aldol, Mannich or umpolung C–O bond-forming reactions. The challenging catalytic asymmetric Mannich reaction of formaldimine equivalent was also realized with moderate enantioselectivities.</description><subject>Aldehydes</subject><subject>Carboxylates</subject><subject>Divergence</subject><subject>Formaldehyde</subject><subject>Hydroxylamine</subject><subject>Ketones</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Optimization</subject><subject>Organic chemistry</subject><subject>Reagents</subject><subject>Stereoselectivity</subject><issn>2052-4129</issn><issn>2052-4110</issn><issn>2052-4129</issn><issn>2052-4110</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNpNkd9KwzAUxosoOOZufIKAd7LoSdKmzaXUvzA2BL0uWZNsHW0zkxasV76Dr-CT-SS2m6Jw4HwHfuc7HL4gOCVwQYCJy2vyuACIwyQ9CEYUIopDQsXhP30cTLzfAAChEYcoHgWfc4Tn1nclRguEl85WVjfrrkTrTjn72pWyKmqNZN54JPtCVVs2hWnrvClsLUtkrKtkqXTP6-nvVAxLUyRrhciUYvsq33RTqMHJt87ZlWz0wKL06_0j3XGDWqClrRUeTIp6hZyWuyv-JDgysvR68tPHwfPtzVN6j2eLu4f0aoZzGokGJ1wA56GQScgUB6INl0YBZ7kCI7RMGCixVIxxCBPIE5PHjCeSREQkYUgpGwdne9-tsy-t9k22sa3rv_QZjWJKgcac9dT5nsqd9d5pk21dUUnXZQSyIYjsLwj2DQPpfPY</recordid><startdate>20210921</startdate><enddate>20210921</enddate><creator>Wu, Binyu</creator><creator>Wen, Xiaolu</creator><creator>Chen, Hongbing</creator><creator>Hu, Lin</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>FR3</scope><scope>JG9</scope><scope>P64</scope><orcidid>https://orcid.org/0000-0002-8600-965X</orcidid></search><sort><creationdate>20210921</creationdate><title>N -Nosyl- O -bromoethyl hydroxylamine acts as a multifunctional formaldehyde, formaldimine, and 1,2-oxazetidine surrogate for C–C and C–O bond-forming reactions</title><author>Wu, Binyu ; Wen, Xiaolu ; Chen, Hongbing ; Hu, Lin</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c259t-86906649a843d601ef6afd063cd0f9ea830d9bd3360480c8fc7368a1519844223</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Aldehydes</topic><topic>Carboxylates</topic><topic>Divergence</topic><topic>Formaldehyde</topic><topic>Hydroxylamine</topic><topic>Ketones</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Optimization</topic><topic>Organic chemistry</topic><topic>Reagents</topic><topic>Stereoselectivity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wu, Binyu</creatorcontrib><creatorcontrib>Wen, Xiaolu</creatorcontrib><creatorcontrib>Chen, Hongbing</creatorcontrib><creatorcontrib>Hu, Lin</creatorcontrib><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Materials Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Organic Chemistry Frontiers</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wu, Binyu</au><au>Wen, Xiaolu</au><au>Chen, Hongbing</au><au>Hu, Lin</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>N -Nosyl- O -bromoethyl hydroxylamine acts as a multifunctional formaldehyde, formaldimine, and 1,2-oxazetidine surrogate for C–C and C–O bond-forming reactions</atitle><jtitle>Organic Chemistry Frontiers</jtitle><date>2021-09-21</date><risdate>2021</risdate><volume>8</volume><issue>18</issue><spage>5124</spage><epage>5129</epage><pages>5124-5129</pages><issn>2052-4129</issn><issn>2052-4110</issn><eissn>2052-4129</eissn><eissn>2052-4110</eissn><abstract>We describe that
N
-nosyl-
O
-bromoethyl hydroxylamine, a bench stable solid, could function as a novel formaldehyde, formaldimine, and 1,2-oxazetidine surrogate under DBU basic conditions. By merely using this simple reagent, a broad range of synthetically useful α-hydroxymethyl and α-aminomethyl ketones, as well as chiral α-alkoxyl and α-aminomethyl indanone carboxylates could be divergently obtained
via
chemo- and stereoselective aldol, Mannich or umpolung C–O bond-forming reactions. The challenging catalytic asymmetric Mannich reaction of formaldimine equivalent was also realized with moderate enantioselectivities.</abstract><cop>London</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/D1QO00748C</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0002-8600-965X</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 2052-4129 |
| ispartof | Organic Chemistry Frontiers, 2021-09, Vol.8 (18), p.5124-5129 |
| issn | 2052-4129 2052-4110 2052-4129 2052-4110 |
| language | eng |
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| source | Royal Society Of Chemistry Journals |
| subjects | Aldehydes Carboxylates Divergence Formaldehyde Hydroxylamine Ketones NMR Nuclear magnetic resonance Optimization Organic chemistry Reagents Stereoselectivity |
| title | N -Nosyl- O -bromoethyl hydroxylamine acts as a multifunctional formaldehyde, formaldimine, and 1,2-oxazetidine surrogate for C–C and C–O bond-forming reactions |
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