Your browser doesn't support javascript.
loading
CAMDOL-enabled diastereoselective synthesis of α-substituted phosphonates.
Huang, Yu; Zhang, Yulong; Pan, Li; Wu, Qian; Li, Ning; Shi, Enxue; Xiao, Junhua.
Afiliación
  • Huang Y; State Key Laboratory of NBC Protection for Civilian, Beijing 102205, China. exshi@sina.com.
  • Zhang Y; State Key Laboratory of NBC Protection for Civilian, Beijing 102205, China. exshi@sina.com.
  • Pan L; State Key Laboratory of NBC Protection for Civilian, Beijing 102205, China. exshi@sina.com.
  • Wu Q; State Key Laboratory of NBC Protection for Civilian, Beijing 102205, China. exshi@sina.com.
  • Li N; State Key Laboratory of NBC Protection for Civilian, Beijing 102205, China. exshi@sina.com.
  • Shi E; State Key Laboratory of NBC Protection for Civilian, Beijing 102205, China. exshi@sina.com.
  • Xiao J; State Key Laboratory of NBC Protection for Civilian, Beijing 102205, China. exshi@sina.com.
Chem Commun (Camb) ; 60(14): 1924-1927, 2024 Feb 13.
Article en En | MEDLINE | ID: mdl-38265054
ABSTRACT
Enantiopure α-substituted phosphonic acids are widely utilized as drugs, pesticides, and ligands. Despite numerous synthetic approaches having been investigated, precise construction of P-adjacent chiral tertiary carbon centres by the employment of recoverable chiral auxiliaries is traditional and still one of the most reliable and practical synthetic methodologies so far. Herein, we present a highly diastereoselective synthesis of α-substituted phosphonates via the unique CAMDOL-derived P-substrates by an efficient sequential deprotonation with LiHMDS and alkylation/arylation with RI. A wide range of 30 structurally diverse α-substituted phosphonate products, including the well-known P-analogues of naproxen and ibuprofen, were thus afforded conveniently in up to 92% yields and 99 1 diastereomeric ratios. The related chiral phosphonic acid could be easily obtained by simple acidic hydrolysis with fully recovered auxiliary. This CAMDOL-enabled asymmetric synthetic protocol exhibits comparative advantages over known chiral-induction methods with easy accessibility and compatibility of furnishing a variety of C-stereogenic centres in the proximity of the phosphorus atom, including some rare examples.

Texto completo: 1 Bases de datos: MEDLINE Tipo de estudio: Guideline Idioma: En Revista: Chem Commun (Camb) Asunto de la revista: QUIMICA Año: 2024 Tipo del documento: Article País de afiliación: China

Texto completo: 1 Bases de datos: MEDLINE Tipo de estudio: Guideline Idioma: En Revista: Chem Commun (Camb) Asunto de la revista: QUIMICA Año: 2024 Tipo del documento: Article País de afiliación: China