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Issue 8, 2017
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Catalyst-controlled regioselectivity in phosphine catalysis: the synthesis of spirocyclic benzofuranones via regiodivergent [3 + 2] annulations of aurones and an allenoate

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Abstract

Catalyst-controlled regiodivergent [3 + 2] annulations of aurones and allenoates have been developed. When a dipeptide phosphine catalyst with an L-D- configuration was employed, α-selective [3 + 2] annulation products could be obtained with good regioselectivities and enantioselectivities. With the employment of L-L- dipeptide phosphines, γ-selective annulation products could be selectively obtained with excellent enantioselectivities. By simply tuning the catalyst configurations, a wide range of α-selective or γ-selective spirocyclic benzofuranones with either aryl or alkyl substitutions could be readily prepared. DFT calculations suggest that the conformation of the dipeptide phosphines influences the hydrogen bonding interactions or the distortion energy, resulting in delicate energy differentiation in the transition states, and accounting for the observed regioselectivity.

Graphical abstract: Catalyst-controlled regioselectivity in phosphine catalysis: the synthesis of spirocyclic benzofuranones via regiodivergent [3 + 2] annulations of aurones and an allenoate

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Publication details

The article was received on 15 May 2017, accepted on 04 Jun 2017 and first published on 12 Jun 2017


Article type: Edge Article
DOI: 10.1039/C7SC02176C
Citation: Chem. Sci., 2017,8, 5699-5704
  • Open access: Creative Commons BY license
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    Catalyst-controlled regioselectivity in phosphine catalysis: the synthesis of spirocyclic benzofuranones via regiodivergent [3 + 2] annulations of aurones and an allenoate

    H. Ni, Z. Yu, W. Yao, Y. Lan, N. Ullah and Y. Lu, Chem. Sci., 2017, 8, 5699
    DOI: 10.1039/C7SC02176C

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