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Quaternary and Tertiary Carbon Centers Synthesized via Gallium-Catalyzed Direct Substitution of Unfunctionalized Propargylic Alcohols with Boronic Acids.
Donald, Clayton P; Boylan, Amy; Nguyen, Truong N; Chen, Po-An; May, Jeremy A.
Affiliation
  • Donald CP; Department of Chemistry, University of Houston, 3585 Cullen Blvd, Fleming Bldg 112, Houston, Texas 77204-5003, United States.
  • Boylan A; Department of Chemistry, University of Houston, 3585 Cullen Blvd, Fleming Bldg 112, Houston, Texas 77204-5003, United States.
  • Nguyen TN; Department of Chemistry, University of Houston, 3585 Cullen Blvd, Fleming Bldg 112, Houston, Texas 77204-5003, United States.
  • Chen PA; Pfizer, 280 Shennecossett Rd, Groton, Connecticut 06340, United States.
  • May JA; Department of Chemistry, University of Houston, 3585 Cullen Blvd, Fleming Bldg 112, Houston, Texas 77204-5003, United States.
Org Lett ; 24(37): 6767-6771, 2022 Sep 23.
Article in En | MEDLINE | ID: mdl-36099564
(IPr)GaCl3/AgSbF6, AgSbF6, and GaCl3 catalyzed substitution of the hydroxyl of secondary and tertiary propargylic alcohols with organoboronic acids via C-C bond formation, and GaCl3 effectively synthesized all-carbon quaternary propargylic centers. These catalysts performed the substitution at carbons bearing alkyl substituents, which has been problematic for other systems. Highly hindered carbon stereocenters were thus produced, including quaternary centers bearing doubly ortho-substituted aryl rings, that are difficult to access with traditional methods.

Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: Org Lett Year: 2022 Document type: Article

Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: Org Lett Year: 2022 Document type: Article