Nine-Membered Benzofuran-Fused Heterocycles: Enantioselective Synthesis by Pd-Catalysis and Rearrangement via Transannular Bond Formation

Zi Qiang Rong; Li Cheng Yang; Song Liu; Zhaoyuan Yu; Ya Nong Wang; Zher Yin Tan; Rui Zhi Huang; Yu Lan; Yu Zhao

doi:10.1021/jacs.7b09161

Nine-Membered Benzofuran-Fused Heterocycles: Enantioselective Synthesis by Pd-Catalysis and Rearrangement via Transannular Bond Formation

Zi Qiang Rong, Li Cheng Yang, Song Liu, Zhaoyuan Yu, Ya Nong Wang, Zher Yin Tan, Rui Zhi Huang, Yu Lan (Lead / Corresponding author), Yu Zhao (Lead / Corresponding author)

Biological Chemistry and Drug Discovery

Research output: Contribution to journal › Article › peer-review

221 Citations (Scopus)

Abstract

The first enantioselective formal [5+4] cycloaddition is realized under palladium catalysis to deliver benzofuran-fused nine-membered rings. These medium-sized heterocycles and derivatives undergo unique rearrangements induced by transannular bond formation, resulting in the production of two classes of densely substituted polycyclic heterocycles in excellent efficiency and stereoselectivity.

Original language	English
Pages (from-to)	15304-15307
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	139
Issue number	43
Early online date	17 Oct 2017
DOIs	https://doi.org/10.1021/jacs.7b09161
Publication status	Published - 1 Nov 2017

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/jacs.7b09161

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abstract = "The first enantioselective formal [5+4] cycloaddition is realized under palladium catalysis to deliver benzofuran-fused nine-membered rings. These medium-sized heterocycles and derivatives undergo unique rearrangements induced by transannular bond formation, resulting in the production of two classes of densely substituted polycyclic heterocycles in excellent efficiency and stereoselectivity.",

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AU - Yang, Li Cheng

AU - Liu, Song

AU - Yu, Zhaoyuan

AU - Wang, Ya Nong

AU - Tan, Zher Yin

AU - Huang, Rui Zhi

AU - Lan, Yu

AU - Zhao, Yu

PY - 2017/11/1

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AB - The first enantioselective formal [5+4] cycloaddition is realized under palladium catalysis to deliver benzofuran-fused nine-membered rings. These medium-sized heterocycles and derivatives undergo unique rearrangements induced by transannular bond formation, resulting in the production of two classes of densely substituted polycyclic heterocycles in excellent efficiency and stereoselectivity.

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Nine-Membered Benzofuran-Fused Heterocycles: Enantioselective Synthesis by Pd-Catalysis and Rearrangement via Transannular Bond Formation

Abstract

ASJC Scopus subject areas

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