Catalytic Asymmetric Addition of Diorganozinc Reagents to N-Phosphinoylalkylimines
The synthesis of α-chiral amines bearing two alkyl groups has been hampered by the accessibility and stability of the alkylimine precursor. Herein, we report an efficient strategy to generate the alkyl-substituted imine in situ that is compatible with the MeDuPHOS monoxide·Cu(I) catalyzed addition o...
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| Published in | Proceedings of the National Academy of Sciences - PNAS Vol. 101; no. 15; pp. 5405 - 5410 |
|---|---|
| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
United States
National Academy of Sciences
13.04.2004
National Acad Sciences |
| Series | Asymmetric Catalysis Special Feature Part I |
| Subjects | |
| Online Access | Get full text |
| ISSN | 0027-8424 1091-6490 |
| DOI | 10.1073/pnas.0307096101 |
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| Abstract | The synthesis of α-chiral amines bearing two alkyl groups has been hampered by the accessibility and stability of the alkylimine precursor. Herein, we report an efficient strategy to generate the alkyl-substituted imine in situ that is compatible with the MeDuPHOS monoxide·Cu(I) catalyzed addition of diorganozinc reagents. The sulfinic acid adduct of the imine is readily prepared by mixing diphenylphosphinic amide, the aldehyde, and sulfinic acid. The sulfinic acid adduct is generally isolated by filtration. The addition of diorganozinc reagents in the presence of Me-DuPHOS monoxide·Cu(I) and the in situ-generated imines affords the corresponding α-chiral amines in high yields and enantiomeric excesses. |
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| AbstractList | The synthesis of {alpha}-chiral amines bearing two alkyl groups has been hampered by the accessibility and stability of the alkylimine precursor. Herein, we report an efficient strategy to generate the alkyl-substituted imine in situ that is compatible with the Me-DuPHOS monoxide-Cu(I) catalyzed addition of diorganozinc reagents. The sulfinic acid adduct of the imine is readily prepared by mixing diphenylphosphinic amide, the aldehyde, and sulfinic acid. The sulfinic acid adduct is generally isolated by filtration. The addition of diorganozinc reagents in the presence of Me-DuPHOS monoxide-Cu(I) and the in situ-generated imines affords the corresponding {alpha}-chiral amines in high yields and enantiomeric excesses. [PERIODICAL ABSTRACT] The synthesis of α-chiral amines bearing two alkyl groups has been hampered by the accessibility and stability of the alkylimine precursor. Herein, we report an efficient strategy to generate the alkyl-substituted imine in situ that is compatible with the MeDuPHOS monoxide·Cu(I) catalyzed addition of diorganozinc reagents. The sulfinic acid adduct of the imine is readily prepared by mixing diphenylphosphinic amide, the aldehyde, and sulfinic acid. The sulfinic acid adduct is generally isolated by filtration. The addition of diorganozinc reagents in the presence of Me-DuPHOS monoxide·Cu(I) and the in situ-generated imines affords the corresponding α-chiral amines in high yields and enantiomeric excesses. The synthesis of α-chiral amines bearing two alkyl groups has been hampered by the accessibility and stability of the alkylimine precursor. Herein, we report an efficient strategy to generate the alkyl-substituted imine in situ that is compatible with the Me-DuPHOS monoxide·Cu(I) catalyzed addition of diorganozinc reagents. The sulfinic acid adduct of the imine is readily prepared by mixing diphenylphosphinic amide, the aldehyde, and sulfinic acid. The sulfinic acid adduct is generally isolated by filtration. The addition of diorganozinc reagents in the presence of Me-DuPHOS monoxide·Cu(I) and the in situ -generated imines affords the corresponding α-chiral amines in high yields and enantiomeric excesses. The synthesis of alpha-chiral amines bearing two alkyl groups has been hampered by the accessibility and stability of the alkylimine precursor. Herein, we report an efficient strategy to generate the alkyl-substituted imine in situ that is compatible with the Me-DuPHOS monoxide.Cu(I) catalyzed addition of diorganozinc reagents. The sulfinic acid adduct of the imine is readily prepared by mixing diphenylphosphinic amide, the aldehyde, and sulfinic acid. The sulfinic acid adduct is generally isolated by filtration. The addition of diorganozinc reagents in the presence of Me-DuPHOS monoxide.Cu(I) and the in situ-generated imines affords the corresponding alpha-chiral amines in high yields and enantiomeric excesses. The synthesis of α-chiral amines bearing two alkyl groups has been hampered by the accessibility and stability of the alkylimine precursor. Herein, we report an efficient strategy to generate the alkyl-substituted imine in situ that is compatible with the Me-DuPHOS monoxide·Cu(I) catalyzed addition of diorganozinc reagents. The sulfinic acid adduct of the imine is readily prepared by mixing diphenylphosphinic amide, the aldehyde, and sulfinic acid. The sulfinic acid adduct is generally isolated by filtration. The addition of diorganozinc reagents in the presence of Me-DuPHOS monoxide·Cu(I) and the in situ -generated imines affords the corresponding α-chiral amines in high yields and enantiomeric excesses. The synthesis of alpha-chiral amines bearing two alkyl groups has been hampered by the accessibility and stability of the alkylimine precursor. Herein, we report an efficient strategy to generate the alkyl-substituted imine in situ that is compatible with the Me-DuPHOS monoxide.Cu(I) catalyzed addition of diorganozinc reagents. The sulfinic acid adduct of the imine is readily prepared by mixing diphenylphosphinic amide, the aldehyde, and sulfinic acid. The sulfinic acid adduct is generally isolated by filtration. The addition of diorganozinc reagents in the presence of Me-DuPHOS monoxide.Cu(I) and the in situ-generated imines affords the corresponding alpha-chiral amines in high yields and enantiomeric excesses.The synthesis of alpha-chiral amines bearing two alkyl groups has been hampered by the accessibility and stability of the alkylimine precursor. Herein, we report an efficient strategy to generate the alkyl-substituted imine in situ that is compatible with the Me-DuPHOS monoxide.Cu(I) catalyzed addition of diorganozinc reagents. The sulfinic acid adduct of the imine is readily prepared by mixing diphenylphosphinic amide, the aldehyde, and sulfinic acid. The sulfinic acid adduct is generally isolated by filtration. The addition of diorganozinc reagents in the presence of Me-DuPHOS monoxide.Cu(I) and the in situ-generated imines affords the corresponding alpha-chiral amines in high yields and enantiomeric excesses. |
| Author | Charette, André B. Boezio, Alessandro A. Côté, Alexandre Halpern, Jack |
| AuthorAffiliation | Department of Chemistry, University of Montreal, P.O. Box 6128, Station Downtown, Montreal, QC, Canada H3C 3J7 |
| AuthorAffiliation_xml | – name: Department of Chemistry, University of Montreal, P.O. Box 6128, Station Downtown, Montreal, QC, Canada H3C 3J7 |
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| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/15064400$$D View this record in MEDLINE/PubMed |
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| Notes | SourceType-Scholarly Journals-1 ObjectType-Feature-1 content type line 14 ObjectType-Article-1 ObjectType-Feature-2 content type line 23 Abbreviation: ee, enantiomeric excess. To whom correspondence should be addressed. E-mail: andre.charette@umontreal.ca. This paper was submitted directly (Track II) to the PNAS office. Edited by Jack Halpern, University of Chicago, Chicago, IL, and approved February 4, 2004 |
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| Snippet | The synthesis of α-chiral amines bearing two alkyl groups has been hampered by the accessibility and stability of the alkylimine precursor. Herein, we report... The synthesis of alpha-chiral amines bearing two alkyl groups has been hampered by the accessibility and stability of the alkylimine precursor. Herein, we... The synthesis of {alpha}-chiral amines bearing two alkyl groups has been hampered by the accessibility and stability of the alkylimine precursor. Herein, we... |
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| StartPage | 5405 |
| SubjectTerms | Adducts Aldehydes Amides Amines Asymmetric Catalysis Special Feature Part I Chemical compounds Copper Imines Ligands Organic chemistry Physical Sciences Reagents Solvents Sulfinic acids |
| Title | Catalytic Asymmetric Addition of Diorganozinc Reagents to N-Phosphinoylalkylimines |
| URI | https://www.jstor.org/stable/3371631 http://www.pnas.org/content/101/15/5405.abstract https://www.ncbi.nlm.nih.gov/pubmed/15064400 https://www.proquest.com/docview/201375871 https://www.proquest.com/docview/71833390 https://pubmed.ncbi.nlm.nih.gov/PMC397394 |
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