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Issue 26, 2019
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A catalytic asymmetric one-pot [3+2] cyclization/semipinacol rearrangement sequence: an efficient construction of a multi-substituted 3H-spiro[benzofuran-2,1′-cyclopentane] skeleton

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Abstract

A facile and efficient method to form a chiral multi-substituted 3H-spiro[benzofuran-2,1′-cyclopentane] structural unit has been developed via a one-pot [3+2] cyclization/semipinacol rearrangement cascade. A catalysis system of Cu(II)/BOX has been used to efficiently construct a key stereogenic center via a cyclization between substituted benzoquinones and allylic alcohols affording the desired products in good yields and with excellent enantioselectivities and diastereoselectivities (21 examples; up to 67% yields; up to 92% ee and up to >20 : 1 dr). This method provides an alternative strategy for the synthesis of the corresponding bioactive molecules containing spiro[benzofurancyclopentane] skeleton units.

Graphical abstract: A catalytic asymmetric one-pot [3+2] cyclization/semipinacol rearrangement sequence: an efficient construction of a multi-substituted 3H-spiro[benzofuran-2,1′-cyclopentane] skeleton

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Article information


Submitted
29 Jan 2019
Accepted
04 Mar 2019
First published
05 Mar 2019

Chem. Commun., 2019,55, 3789-3792
Article type
Communication

A catalytic asymmetric one-pot [3+2] cyclization/semipinacol rearrangement sequence: an efficient construction of a multi-substituted 3H-spiro[benzofuran-2,1′-cyclopentane] skeleton

L. Liu, L. Lei, Z. Zhan, S. Liu, Y. Wang, Y. Tu, F. Zhang, X. Zhang, A. Ma and S. Wang, Chem. Commun., 2019, 55, 3789
DOI: 10.1039/C9CC00811J

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