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Chiral phosphine-mediated intramolecular [3 + 2] annulation: enhanced enantioselectivity by achiral Bronsted acid.

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 Brønsted 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 Brønsted acids/chiral phosphines could more efficiently distinguish between two enantioselective pathways, thus leading to enhanced enantioselectivity.

SUBMITTER: Yao W

PROVIDER: S-EPMC5618691 | biostudies-other | 2017 Jul

REPOSITORIES: biostudies-other

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Chiral phosphine-mediated intramolecular [3 + 2] annulation: enhanced enantioselectivity by achiral Brønsted acid.

Yao Weijun W Yu Zhaoyuan Z Wen Shan S Ni Huanzhen H Ullah Nisar N Lan Yu Y Lu Yixin Y

Chemical science 20170517 7

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 Brønsted 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 Brønsted acids/chiral phosphines could more effi ...[more]

PMID: 28970906

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