Chiral phosphine-mediated intramolecular [3 + 2] annulation: enhanced enantioselectivity by achiral Br?nsted acid?
Chemical Science Pub Date: 2017-05-17 DOI: 10.1039/C7SC00952F
Abstract
Enantioselective intramolecular [3 + 2] annulation of chalcones bearing an allene moiety has been successfully developed. The reaction was effectively promoted by amino acid-derived phosphines, in combination with achiral Br?nsted acids. Dihydrocoumarin architectures were constructed in high yields and with excellent enantiomeric excesses. Theoretical studies via DFT calculations revealed that the hydrogen bonding network induced by achiral Br?nsted acids/chiral phosphines could more efficiently distinguish between two enantioselective pathways, thus leading to enhanced enantioselectivity.
![Graphical abstract: Chiral phosphine-mediated intramolecular [3 + 2] annulation: enhanced enantioselectivity by achiral Br?nsted acid](http://scimg.chem960.com/usr/1/C7SC00952F.jpg)
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Journal Name：Chemical Science
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CAS no.: 89640-58-4
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