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

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...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2019-03, Vol.55 (26), p.3789-3792
Main Authors: Liu, Lin, Lei, Lin-Sheng, Zhan, Zong-Song, Liu, Si-Zhan, Wang, Yu-Xiao, Tu, Yong-Qiang, Zhang, Fu-Min, Zhang, Xiao-Ming, Ma, Ai-Jun, Wang, Shao-Hua
Format: Article
Language:English
Subjects:
Alcohols
Catalysis
Chemical synthesis
Crystallography
Direct reduction
Substitutes
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Summary: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.
ISSN:1359-7345
1364-548X
DOI:10.1039/c9cc00811j