Forschungsartikel
Chiral Phosphoric Acid Dual-Function Catalysis: Asymmetric Allylation with α-Vinyl Allylboron Reagents
Shang Gao,
Meng Duan,
Prof. Dr. Kendall N. Houk,
Prof. Dr. Ming Chen,
Shang Gao
Department of Chemistry and Biochemistry, Auburn University, Auburn, AL, 36849 USA
These authors contributed equally to this work.
Search for more papers by this authorMeng Duan
Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, CA, 90095 USA
These authors contributed equally to this work.
Search for more papers by this authorCorresponding Author
Prof. Dr. Kendall N. Houk
Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, CA, 90095 USA
Search for more papers by this authorCorresponding Author
Prof. Dr. Ming Chen
Department of Chemistry and Biochemistry, Auburn University, Auburn, AL, 36849 USA
Search for more papers by this authorShang Gao,
Meng Duan,
Prof. Dr. Kendall N. Houk,
Prof. Dr. Ming Chen,
Shang Gao
Department of Chemistry and Biochemistry, Auburn University, Auburn, AL, 36849 USA
These authors contributed equally to this work.
Search for more papers by this authorMeng Duan
Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, CA, 90095 USA
These authors contributed equally to this work.
Search for more papers by this authorCorresponding Author
Prof. Dr. Kendall N. Houk
Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, CA, 90095 USA
Search for more papers by this authorCorresponding Author
Prof. Dr. Ming Chen
Department of Chemistry and Biochemistry, Auburn University, Auburn, AL, 36849 USA
Search for more papers by this authorDedicated to Professor William R. Roush
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.
Conflict of interest
The authors declare no conflict of interest.
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