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- Title
Chiral Phosphoric Acid Dual‐Function Catalysis: Asymmetric Allylation with α‐Vinyl Allylboron Reagents.
- Authors
Gao, Shang; Duan, Meng; Houk, Kendall N.; Chen, Ming
- Abstract
We report a dual function asymmetric catalysis by a chiral phosphoric acid catalyst that controls both enantioselective addition of an achiral α‐vinyl allylboronate to aldehydes and pseudo‐axial orientation of the α‐vinyl group in the transition state. The reaction produces dienyl homoallylic alcohols with high Z‐selectivities and enantioselectivities. Computational studies revealed that minimization of steric interactions between the alkyl groups of the diol on boron and the chiral phosphoric acid catalyst influence the orientation of α‐vinyl substituent of the allylboronate reagent to occupy a pseudo‐axial position in the transition state.
- Subjects
DIALKYLZINC; CATALYSIS; PHOSPHORIC acid; ALLYLATION; ACID catalysts; ENANTIOSELECTIVE catalysis; ALKYL group; GLYCOLS
- Publication
Angewandte Chemie, 2020, Vol 132, Issue 26, p10627
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.202000039