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(2-Formyl-1-phenylcyclopropyl)phosphonates as building blocks for (2-aminomethyl-cyclopropyl)phosphonates
A diastereomeric mixture of dimethyl (2-formyl-2-methyl-1-phenylcyclopropyl)phosphonate (( Z)- 6, ( E)- 6) was obtained by thermally induced cyclopropanation of α-methylacrolein with α-diazobenzylphosphonate 5. Application of proline or proline-derived organocatalysts accelerated the reaction, but h...
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| Published in: | Tetrahedron 2011-04, Vol.67 (16), p.2849-2857 |
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| Main Authors: | , |
| Format: | Article |
| Language: | English |
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| container_end_page | 2857 |
| container_issue | 16 |
| container_start_page | 2849 |
| container_title | Tetrahedron |
| container_volume | 67 |
| creator | El-Gokha, Ahmed Maas, Gerhard |
| description | A diastereomeric mixture of dimethyl (2-formyl-2-methyl-1-phenylcyclopropyl)phosphonate ((
Z)-
6, (
E)-
6) was obtained by thermally induced cyclopropanation of α-methylacrolein with α-diazobenzylphosphonate
5. Application of proline or proline-derived organocatalysts accelerated the reaction, but had a minor effect on the
Z/
E ratio of
6. By reaction with benzylamine or methyl esters of glycine, (
S)-alanine, and (
S)-phenylalanine, the
Z/
E-mixture of
6 was converted into cyclopropylaldimines, which after reduction gave the corresponding
N-substituted (2-aminomethyl-cyclopropyl)phosphonates.
[Display omitted] |
| doi_str_mv | 10.1016/j.tet.2011.02.068 |
| format | article |
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Z)-
6, (
E)-
6) was obtained by thermally induced cyclopropanation of α-methylacrolein with α-diazobenzylphosphonate
5. Application of proline or proline-derived organocatalysts accelerated the reaction, but had a minor effect on the
Z/
E ratio of
6. By reaction with benzylamine or methyl esters of glycine, (
S)-alanine, and (
S)-phenylalanine, the
Z/
E-mixture of
6 was converted into cyclopropylaldimines, which after reduction gave the corresponding
N-substituted (2-aminomethyl-cyclopropyl)phosphonates.
[Display omitted]</description><identifier>ISSN: 0040-4020</identifier><identifier>EISSN: 1464-5416</identifier><identifier>DOI: 10.1016/j.tet.2011.02.068</identifier><identifier>CODEN: TETRAB</identifier><language>eng</language><publisher>Kidlington: Elsevier Ltd</publisher><subject>(Aminoalkyl)phosphonates ; Acceptor-substituted cyclopropanes ; Alicyclic compounds ; Alicyclic compounds, terpenoids, prostaglandins, steroids ; Amino acids ; Catalysis ; Catalysts: preparations and properties ; Chemistry ; Cyclopropylphosphonates ; Dimethyl ; Esters ; Exact sciences and technology ; General and physical chemistry ; Glycine ; Organic chemistry ; Organocatalysis ; Preparations and properties ; Proline ; Reduction ; Tetrahedrons ; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry</subject><ispartof>Tetrahedron, 2011-04, Vol.67 (16), p.2849-2857</ispartof><rights>2011 Elsevier Ltd</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c360t-48311e2e20224a04d761d2446400a79aa5a1d097f52923f12118649fcf09b4663</citedby><cites>FETCH-LOGICAL-c360t-48311e2e20224a04d761d2446400a79aa5a1d097f52923f12118649fcf09b4663</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=24045847$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>El-Gokha, Ahmed</creatorcontrib><creatorcontrib>Maas, Gerhard</creatorcontrib><title>(2-Formyl-1-phenylcyclopropyl)phosphonates as building blocks for (2-aminomethyl-cyclopropyl)phosphonates</title><title>Tetrahedron</title><description>A diastereomeric mixture of dimethyl (2-formyl-2-methyl-1-phenylcyclopropyl)phosphonate ((
Z)-
6, (
E)-
6) was obtained by thermally induced cyclopropanation of α-methylacrolein with α-diazobenzylphosphonate
5. Application of proline or proline-derived organocatalysts accelerated the reaction, but had a minor effect on the
Z/
E ratio of
6. By reaction with benzylamine or methyl esters of glycine, (
S)-alanine, and (
S)-phenylalanine, the
Z/
E-mixture of
6 was converted into cyclopropylaldimines, which after reduction gave the corresponding
N-substituted (2-aminomethyl-cyclopropyl)phosphonates.
[Display omitted]</description><subject>(Aminoalkyl)phosphonates</subject><subject>Acceptor-substituted cyclopropanes</subject><subject>Alicyclic compounds</subject><subject>Alicyclic compounds, terpenoids, prostaglandins, steroids</subject><subject>Amino acids</subject><subject>Catalysis</subject><subject>Catalysts: preparations and properties</subject><subject>Chemistry</subject><subject>Cyclopropylphosphonates</subject><subject>Dimethyl</subject><subject>Esters</subject><subject>Exact sciences and technology</subject><subject>General and physical chemistry</subject><subject>Glycine</subject><subject>Organic chemistry</subject><subject>Organocatalysis</subject><subject>Preparations and properties</subject><subject>Proline</subject><subject>Reduction</subject><subject>Tetrahedrons</subject><subject>Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry</subject><issn>0040-4020</issn><issn>1464-5416</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><recordid>eNp9kDFPwzAQhS0EEqXwA9iyIJUh4c5xnEZMqKKAVIkFZst1HOrixMFOkfLvcdWKDYbTLe99d-8Rco2QISC_22aDHjIKiBnQDPj8hEyQcZYWDPkpmQAwSBlQOCcXIWwBopLmE2JmNF063442xbTf6G60alTW9d71o73tNy7E6eSgQyJDst4ZW5vuI1lbpz5D0jifRIJsTedaPWwi5i_7JTlrpA366rin5H35-LZ4TlevTy-Lh1Wqcg5DyuY5oqaaAqVMAqtLjjVlMQqALCspC4k1VGVT0IrmDVLEOWdVoxqo1ozzfEpmB2784WunwyBaE5S2Vnba7YLAMsLKnJdllOJBqrwLwetG9N600o8CQexrFVsRaxX7WgVQEWuNnpsjXgYlbeNlp0z4NVIGrJizPfv-oNMx67fRXgRldKd0bbxWg6id-efKD3fujT0</recordid><startdate>20110422</startdate><enddate>20110422</enddate><creator>El-Gokha, Ahmed</creator><creator>Maas, Gerhard</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>20110422</creationdate><title>(2-Formyl-1-phenylcyclopropyl)phosphonates as building blocks for (2-aminomethyl-cyclopropyl)phosphonates</title><author>El-Gokha, Ahmed ; Maas, Gerhard</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c360t-48311e2e20224a04d761d2446400a79aa5a1d097f52923f12118649fcf09b4663</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>(Aminoalkyl)phosphonates</topic><topic>Acceptor-substituted cyclopropanes</topic><topic>Alicyclic compounds</topic><topic>Alicyclic compounds, terpenoids, prostaglandins, steroids</topic><topic>Amino acids</topic><topic>Catalysis</topic><topic>Catalysts: preparations and properties</topic><topic>Chemistry</topic><topic>Cyclopropylphosphonates</topic><topic>Dimethyl</topic><topic>Esters</topic><topic>Exact sciences and technology</topic><topic>General and physical chemistry</topic><topic>Glycine</topic><topic>Organic chemistry</topic><topic>Organocatalysis</topic><topic>Preparations and properties</topic><topic>Proline</topic><topic>Reduction</topic><topic>Tetrahedrons</topic><topic>Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>El-Gokha, Ahmed</creatorcontrib><creatorcontrib>Maas, Gerhard</creatorcontrib><collection>Pascal-Francis</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Tetrahedron</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>El-Gokha, Ahmed</au><au>Maas, Gerhard</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>(2-Formyl-1-phenylcyclopropyl)phosphonates as building blocks for (2-aminomethyl-cyclopropyl)phosphonates</atitle><jtitle>Tetrahedron</jtitle><date>2011-04-22</date><risdate>2011</risdate><volume>67</volume><issue>16</issue><spage>2849</spage><epage>2857</epage><pages>2849-2857</pages><issn>0040-4020</issn><eissn>1464-5416</eissn><coden>TETRAB</coden><abstract>A diastereomeric mixture of dimethyl (2-formyl-2-methyl-1-phenylcyclopropyl)phosphonate ((
Z)-
6, (
E)-
6) was obtained by thermally induced cyclopropanation of α-methylacrolein with α-diazobenzylphosphonate
5. Application of proline or proline-derived organocatalysts accelerated the reaction, but had a minor effect on the
Z/
E ratio of
6. By reaction with benzylamine or methyl esters of glycine, (
S)-alanine, and (
S)-phenylalanine, the
Z/
E-mixture of
6 was converted into cyclopropylaldimines, which after reduction gave the corresponding
N-substituted (2-aminomethyl-cyclopropyl)phosphonates.
[Display omitted]</abstract><cop>Kidlington</cop><pub>Elsevier Ltd</pub><doi>10.1016/j.tet.2011.02.068</doi><tpages>9</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0040-4020 |
| ispartof | Tetrahedron, 2011-04, Vol.67 (16), p.2849-2857 |
| issn | 0040-4020 1464-5416 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1744673677 |
| source | Elsevier |
| subjects | (Aminoalkyl)phosphonates Acceptor-substituted cyclopropanes Alicyclic compounds Alicyclic compounds, terpenoids, prostaglandins, steroids Amino acids Catalysis Catalysts: preparations and properties Chemistry Cyclopropylphosphonates Dimethyl Esters Exact sciences and technology General and physical chemistry Glycine Organic chemistry Organocatalysis Preparations and properties Proline Reduction Tetrahedrons Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry |
| title | (2-Formyl-1-phenylcyclopropyl)phosphonates as building blocks for (2-aminomethyl-cyclopropyl)phosphonates |
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