Asymmetric synthesis of 3,4-anti- and 3,4-syn-substituted aminopyrrolidines via lithium amide conjugate addition.
The diastereoselective conjugate addition of homochiral lithium amides to methyl 4-(N-allyl-N-benzylamino)but-2-enoate has been used as the key step in a simple and efficient protocol for the preparation of 3,4-substituted aminopyrrolidines. This protocol provides a complementary and stereoselective...
| Main Authors: | , , , , , , , , |
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| Format: | Journal article |
| Language: | English |
| Published: |
2007
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| _version_ | 1797093209096060928 |
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| author | Davies, S Garner, A Goddard, E Kruchinin, D Roberts, P Smith, A Rodriguez-Solla, H Thomson, J Toms, S |
| author_facet | Davies, S Garner, A Goddard, E Kruchinin, D Roberts, P Smith, A Rodriguez-Solla, H Thomson, J Toms, S |
| author_sort | Davies, S |
| collection | OXFORD |
| description | The diastereoselective conjugate addition of homochiral lithium amides to methyl 4-(N-allyl-N-benzylamino)but-2-enoate has been used as the key step in a simple and efficient protocol for the preparation of 3,4-substituted aminopyrrolidines. This protocol provides a complementary and stereoselective route to both anti- and syn-3-amino-4-alkylpyrrolidines as well as anti- and syn-3-hydroxy-4-aminopyrrolidines, in high de and ee viabeta-amino enolate functionalisation. This methodology has been applied to the synthesis of anti-(3S,4S)- and syn-(3R,4S)-3-methoxy-4-(N-methylamino)pyrrolidine. |
| first_indexed | 2024-03-07T03:57:00Z |
| format | Journal article |
| id | oxford-uuid:c3378b3f-26ea-4a9a-b30f-b7f44bb11ebd |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T03:57:00Z |
| publishDate | 2007 |
| record_format | dspace |
| spelling | oxford-uuid:c3378b3f-26ea-4a9a-b30f-b7f44bb11ebd2022-03-27T06:14:47ZAsymmetric synthesis of 3,4-anti- and 3,4-syn-substituted aminopyrrolidines via lithium amide conjugate addition.Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:c3378b3f-26ea-4a9a-b30f-b7f44bb11ebdEnglishSymplectic Elements at Oxford2007Davies, SGarner, AGoddard, EKruchinin, DRoberts, PSmith, ARodriguez-Solla, HThomson, JToms, SThe diastereoselective conjugate addition of homochiral lithium amides to methyl 4-(N-allyl-N-benzylamino)but-2-enoate has been used as the key step in a simple and efficient protocol for the preparation of 3,4-substituted aminopyrrolidines. This protocol provides a complementary and stereoselective route to both anti- and syn-3-amino-4-alkylpyrrolidines as well as anti- and syn-3-hydroxy-4-aminopyrrolidines, in high de and ee viabeta-amino enolate functionalisation. This methodology has been applied to the synthesis of anti-(3S,4S)- and syn-(3R,4S)-3-methoxy-4-(N-methylamino)pyrrolidine. |
| spellingShingle | Davies, S Garner, A Goddard, E Kruchinin, D Roberts, P Smith, A Rodriguez-Solla, H Thomson, J Toms, S Asymmetric synthesis of 3,4-anti- and 3,4-syn-substituted aminopyrrolidines via lithium amide conjugate addition. |
| title | Asymmetric synthesis of 3,4-anti- and 3,4-syn-substituted aminopyrrolidines via lithium amide conjugate addition. |
| title_full | Asymmetric synthesis of 3,4-anti- and 3,4-syn-substituted aminopyrrolidines via lithium amide conjugate addition. |
| title_fullStr | Asymmetric synthesis of 3,4-anti- and 3,4-syn-substituted aminopyrrolidines via lithium amide conjugate addition. |
| title_full_unstemmed | Asymmetric synthesis of 3,4-anti- and 3,4-syn-substituted aminopyrrolidines via lithium amide conjugate addition. |
| title_short | Asymmetric synthesis of 3,4-anti- and 3,4-syn-substituted aminopyrrolidines via lithium amide conjugate addition. |
| title_sort | asymmetric synthesis of 3 4 anti and 3 4 syn substituted aminopyrrolidines via lithium amide conjugate addition |
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