Versatile Cobalt-Catalyzed Enantioselective Entry to Boryl-Functionalized All-Carbon Quaternary Stereogenic Centers

• Published in: Journal of the American Chemical Society Vol. 140; no. 34; pp. 10687 - 10690
• Main Authors: Wang, Chao, Ge, Shaozhong
• Format: Journal Article
• Language: English
• 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

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...