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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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 140; no. 34; pp. 10687 - 10690
Main Authors Wang, Chao, Ge, Shaozhong
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 29.08.2018
Amer Chemical Soc
Subjects
amides
amino acids
Chemistry
Chemistry, Multidisciplinary
enantioselectivity
Physical Sciences
Science & Technology
1,6-ENYNES
RHODIUM
NATURAL-PRODUCTS
STEREOCENTERS
GAMMA-LACTAMS
ENYNE CYCLOISOMERIZATION
ALDEHYDES
ASYMMETRIC HYDROGENATION
C-H FUNCTIONALIZATION
REDUCTIVE CYCLIZATION
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Summary: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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/jacs.8b06814