| Enantioselective synthesis of alpha-substituted ketones by asymmetric addition of chiral zinc enamides to 1-alkenes. | |
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MedLine Citation:
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PMID: 12785764 Owner: NLM Status: PubMed-not-MEDLINE |
Abstract/OtherAbstract:
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A zinc enamide of a chiral imine derived from a ketone and (S)-valinol or (S)-t-leucinol undergoes addition to 1-alkene to generate a gamma-zincioimine intermediate, which reacts with a carbon electrophile to give upon hydrolysis an optically active alpha-substituted ketone in good yield. The stereoselectivity of the addition reaction may reach 99% for the reaction of a cyclohexanone imine with ethylene. |
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Authors:
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Masaharu Nakamura; Takuji Hatakeyama; Kenji Hara; Eiichi Nakamura |
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Publication Detail:
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Type: Journal Article |
Journal Detail:
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Title: Journal of the American Chemical Society Volume: 125 ISSN: 0002-7863 ISO Abbreviation: J. Am. Chem. Soc. Publication Date: 2003 May |
Date Detail:
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Created Date: 2003-06-05 Completed Date: 2003-07-10 Revised Date: 2008-01-17 |
Medline Journal Info:
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Nlm Unique ID: 7503056 Medline TA: J Am Chem Soc Country: United States |
Other Details:
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Languages: eng Pagination: 6362-3 Citation Subset: - |
Affiliation:
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Department of Chemistry, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan. |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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