Versatile Cobalt-Catalyzed Enantioselective Entry to Boryl-Functionalized All-Carbon Quaternary Stereogenic Centers
We report an asymmetric synthesis of chiral boryl-functionalized γ-lactams containing all-carbon quaternary stereocenters via a Co-catalyzed enantioselective hydroboration/cyclization of amide-tethered 1,6-enynes. These enantio-enriched γ-lactam products can be readily converted to a variety of cycl...
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| Published in | Journal of the American Chemical Society Vol. 140; no. 34; pp. 10687 - 10690 |
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| Main Authors | , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
29.08.2018
Amer Chemical Soc |
| Subjects | |
| Online Access | Get full text |
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| Abstract | We report an asymmetric synthesis of chiral boryl-functionalized γ-lactams containing all-carbon quaternary stereocenters via a Co-catalyzed enantioselective hydroboration/cyclization of amide-tethered 1,6-enynes. These enantio-enriched γ-lactam products can be readily converted to a variety of cyclic and acyclic other chiral γ-lactams, pyrrolidin-2,3-diones, β-amino acid N-carboxyanhydrides, and β-amino carboxylic amides. |
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| AbstractList | We report an asymmetric synthesis of chiral boryl-functionalized gamma-lactams containing all-carbon quaternary stereocenters via a Co-catalyzed enantioselective hydroboration/cyclization of amide-tethered 1,6-enynes. These enantio-enriched gamma-lactam products can be readily converted to a variety of cyclic and acyclic other chiral gamma-lactams, pyrrolidin-2,3-diones, beta-amino acid N-carboxyanhydrides, and beta-amino carboxylic amides. We report an asymmetric synthesis of chiral boryl-functionalized γ-lactams containing all-carbon quaternary stereocenters via a Co-catalyzed enantioselective hydroboration/cyclization of amide-tethered 1,6-enynes. These enantio-enriched γ-lactam products can be readily converted to a variety of cyclic and acyclic other chiral γ-lactams, pyrrolidin-2,3-diones, β-amino acid N-carboxyanhydrides, and β-amino carboxylic amides.We report an asymmetric synthesis of chiral boryl-functionalized γ-lactams containing all-carbon quaternary stereocenters via a Co-catalyzed enantioselective hydroboration/cyclization of amide-tethered 1,6-enynes. These enantio-enriched γ-lactam products can be readily converted to a variety of cyclic and acyclic other chiral γ-lactams, pyrrolidin-2,3-diones, β-amino acid N-carboxyanhydrides, and β-amino carboxylic amides. We report an asymmetric synthesis of chiral boryl-functionalized γ-lactams containing all-carbon quaternary stereocenters via a Co-catalyzed enantioselective hydroboration/cyclization of amide-tethered 1,6-enynes. These enantio-enriched γ-lactam products can be readily converted to a variety of cyclic and acyclic other chiral γ-lactams, pyrrolidin-2,3-diones, β-amino acid N-carboxyanhydrides, and β-amino carboxylic amides. |
| Author | Wang, Chao Ge, Shaozhong |
| AuthorAffiliation | Department of Chemistry |
| AuthorAffiliation_xml | – name: Department of Chemistry |
| Author_xml | – sequence: 1 givenname: Chao orcidid: 0000-0001-6979-8506 surname: Wang fullname: Wang, Chao – sequence: 2 givenname: Shaozhong orcidid: 0000-0003-1045-1940 surname: Ge fullname: Ge, Shaozhong email: chmgsh@nus.edu.sg |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/30114355$$D View this record in MEDLINE/PubMed |
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| Keywords | 1,6-ENYNES RHODIUM NATURAL-PRODUCTS STEREOCENTERS GAMMA-LACTAMS ENYNE CYCLOISOMERIZATION ALDEHYDES ASYMMETRIC HYDROGENATION C-H FUNCTIONALIZATION REDUCTIVE CYCLIZATION |
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| Snippet | We report an asymmetric synthesis of chiral boryl-functionalized γ-lactams containing all-carbon quaternary stereocenters via a Co-catalyzed enantioselective... We report an asymmetric synthesis of chiral boryl-functionalized gamma-lactams containing all-carbon quaternary stereocenters via a Co-catalyzed... |
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| SubjectTerms | amides amino acids Chemistry Chemistry, Multidisciplinary enantioselectivity Physical Sciences Science & Technology |
| Title | Versatile Cobalt-Catalyzed Enantioselective Entry to Boryl-Functionalized All-Carbon Quaternary Stereogenic Centers |
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