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Asymmetric Hydrative Aldol Reaction (HAR) via Vinyl-Gold Promoted Intermolecular Ynamide Addition to Aldehydes.
Yuan, Teng; Radefeld, Kelton; Shan, Chuan; Wegner, Carter; Nichols, Erin; Ye, Xiaohan; Tang, Qi; Wojtas, Lukasz; Shi, Xiaodong.
Affiliation
  • Yuan T; Department of Chemistry, University of South Florida, FL 33620, Tampa, USA.
  • Radefeld K; Department of Chemistry, University of South Florida, FL 33620, Tampa, USA.
  • Shan C; Department of Chemistry, University of South Florida, FL 33620, Tampa, USA.
  • Wegner C; Department of Chemistry, University of South Florida, FL 33620, Tampa, USA.
  • Nichols E; Department of Chemistry, University of South Florida, FL 33620, Tampa, USA.
  • Ye X; Department of Chemistry, University of South Florida, FL 33620, Tampa, USA.
  • Tang Q; Department of Chemistry, University of South Florida, FL 33620, Tampa, USA.
  • Wojtas L; Department of Chemistry, University of South Florida, FL 33620, Tampa, USA.
  • Shi X; Department of Chemistry, University of South Florida, FL 33620, Tampa, USA.
Angew Chem Int Ed Engl ; 62(31): e202305810, 2023 Aug 01.
Article in En | MEDLINE | ID: mdl-37276357
ABSTRACT
Herein, we reported an intermolecular asymmetric hydrative aldol reaction through vinyl-gold intermediate under ambient conditions. This tandem alkyne hydration and sequential nucleophilic addition afforded a "base-free" approach to ß-hydroxy amides with high efficiency (up to 95 % yields, >50 examples). Vinyl gold intermediate was applied as reactive nucleophile and Fe(acac)3 was used as the critical co-catalyst to prevent undesired protodeauration, allowing this transformation to proceed under mild conditions with good functional group tolerance and excellent stereoselectivity (>20 1 d.r. and up to 99 % ee).
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Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: Angew Chem Int Ed Engl Year: 2023 Document type: Article Affiliation country:
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Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: Angew Chem Int Ed Engl Year: 2023 Document type: Article Affiliation country: