Wittig/BâH insertion reaction: A unique access to trisubstituted Z-alkenes.
Sci Adv
; 9(37): eadj2486, 2023 Sep 15.
Article
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| MEDLINE
| ID: mdl-37703379
ABSTRACT
The Wittig reaction, which is one of the most effective methods for synthesizing alkenes from carbonyl compounds, generally gives thermodynamically stable E-alkenes, and synthesis of trisubstituted Z-alkenes from ketones presents notable challenges. Here, we report what we refer to as Wittig/BâH insertion reactions, which innovatively combine a Wittig reaction with carbene insertion into a BâH bond and constitute a promising method for the synthesis of thermodynamically unstable trisubstituted Z-boryl alkenes. Combined with the easy transformations of boryl group, this methodology provides efficient access to a variety of previously unavailable trisubstituted Z-alkenes and thus provides a platform for discovery of pharmaceuticals. The unique Z-selectivity of the reaction is determined by the maximum overlap of the orbitals between the BâH bond of the borane adduct and the alkylidene carbene intermediate in the transition state.
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1
Colección:
01-internacional
Base de datos:
MEDLINE
Idioma:
En
Revista:
Sci Adv
Año:
2023
Tipo del documento:
Article
País de afiliación:
China