| Diastereoselective conjugate additions to pi-allylmolybdenum complexes: a stereocontrolled route to 3,4,5-trisubstituted gamma-butyrolactones. | |
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MedLine Citation:
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PMID: 12049502 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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[reaction: see text] pi-Allylmolybdenum complex 6b is obtained as a single isomer by Knoevenagel condensation of aldehyde 1 with Meldrum's acid. Conjugate additions of Grignard reagents to Meldrum's acid alkylidene derivative 6b are shown to be completely diastereoselective. Further functional group transformation of the 1,4-adducts, followed by demetalation, leads to trisubstituted tetrahydrofurans and gamma-butyrolactones. Whereas the synthesis of tetrahydrofurans (X = 2H) is not completely stereoselective, the gamma-butyrolactones (X = O) are obtained with good to excellent diastereoselectivities. |
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Authors:
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Anthony J Pearson; Eugen F Mesaros |
Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, P.H.S. |
Journal Detail:
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Title: Organic letters Volume: 4 ISSN: 1523-7060 ISO Abbreviation: Org. Lett. Publication Date: 2002 Jun |
Date Detail:
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Created Date: 2002-06-06 Completed Date: 2002-07-24 Revised Date: 2007-11-14 |
Medline Journal Info:
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Nlm Unique ID: 100890393 Medline TA: Org Lett Country: United States |
Other Details:
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Languages: eng Pagination: 2001-4 Citation Subset: IM |
Affiliation:
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Department of Chemistry, Case Western Reserve University, Cleveland, Ohio 44106, USA. ajp4@po.cwru.edu |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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4-Butyrolactone
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chemical synthesis* Molybdenum / chemistry* Stereoisomerism |
| Grant Support | |
ID/Acronym/Agency:
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GM49221/GM/NIGMS NIH HHS |
| Chemical | |
Reg. No./Substance:
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7439-98-7/Molybdenum; 96-48-0/4-Butyrolactone |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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