Novel Carbonyl Bromoallylation/Heck Reaction Sequence. Stereocontrolled Access to Bicyclic β-Lactams
The reaction of 2,3-dibromopropene with racemic as well as enantiopure 4-oxoazetidine-2-carbaldehydes 1 in aqueous media was promoted by tin in the presence of several additives to afford the corresponding bromohomoallyl alcohols 2 in high diastereoselectivities. However, indium or zinc were unable...
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| Veröffentlicht in: | Journal of organic chemistry 2005-04, Vol.70 (7), p.2713-2719 |
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| container_end_page | 2719 |
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| container_issue | 7 |
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| container_title | Journal of organic chemistry |
| container_volume | 70 |
| creator | Alcaide, Benito Almendros, Pedro Rodríguez-Acebes, Raquel |
| description | The reaction of 2,3-dibromopropene with racemic as well as enantiopure 4-oxoazetidine-2-carbaldehydes 1 in aqueous media was promoted by tin in the presence of several additives to afford the corresponding bromohomoallyl alcohols 2 in high diastereoselectivities. However, indium or zinc were unable to promote the bromoallylation reaction of aldehydes 1 under similar Barbier-type conditions. Vinyl bromides 2 bearing an extra alkene tether were used for the preparation of differently sized, fused bicyclic β-lactams of nonconventional structure via Heck cyclization. |
| doi_str_mv | 10.1021/jo0478306 |
| format | Article |
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Stereocontrolled Access to Bicyclic β-Lactams</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>The reaction of 2,3-dibromopropene with racemic as well as enantiopure 4-oxoazetidine-2-carbaldehydes 1 in aqueous media was promoted by tin in the presence of several additives to afford the corresponding bromohomoallyl alcohols 2 in high diastereoselectivities. However, indium or zinc were unable to promote the bromoallylation reaction of aldehydes 1 under similar Barbier-type conditions. Vinyl bromides 2 bearing an extra alkene tether were used for the preparation of differently sized, fused bicyclic β-lactams of nonconventional structure via Heck cyclization.</description><subject>beta-Lactams - chemistry</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with only one n hetero atom and condensed derivatives</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Spectrophotometry, Infrared</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkMFuEzEQhi0EoqFw4AWQLyD1sK3XXtu7xzaUBjUqiJSzNTuZSNt61629QeS1eBCeqY4SNZeOZI1G_vzP75-xj6U4LYUsz-6CqGythHnFJqWWojCNqF6ziRBSFkoadcTepXQncmmt37KjUtvaalNNGN2EP-T5FGIbho3nFzH0AbzfeBi7MJzNCO_5LwLcTnxBj2sakE75YqRIAcMwxuA9Lfk5IqXEx8AvOtyg75D__1fM80Po03v2ZgU-0Yd9P2a_v13eTmfF_MfV9-n5vABVl2OhWqPMykoLZYWk9HJZN42UEqGC1qo2H9BYNcKQIF0rWbX5_8bKpqlqYUEdsy873YcYstM0ur5LSN7DQGGdnLFaS12LDJ7sQIwhpUgr9xC7HuLGlcJtM3XPmWb201503fa0PJD7EDPweQ9AQvCrCAN26cAZoxprt0uLHdelkf4-30O8z8aU1e7258KZevb1-qaRTh50AVP2s45Dzu4Fg0-tgJkK</recordid><startdate>20050401</startdate><enddate>20050401</enddate><creator>Alcaide, Benito</creator><creator>Almendros, Pedro</creator><creator>Rodríguez-Acebes, Raquel</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</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>20050401</creationdate><title>Novel Carbonyl Bromoallylation/Heck Reaction Sequence. 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| ispartof | Journal of organic chemistry, 2005-04, Vol.70 (7), p.2713-2719 |
| issn | 0022-3263 1520-6904 |
| language | eng |
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| source | MEDLINE; ACS Publications |
| subjects | beta-Lactams - chemistry Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Magnetic Resonance Spectroscopy Organic chemistry Preparations and properties Spectrophotometry, Infrared |
| title | Novel Carbonyl Bromoallylation/Heck Reaction Sequence. Stereocontrolled Access to Bicyclic β-Lactams |
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