Construction of Nine-Membered Heterocycles through Palladium-Catalyzed Formal [5+4] Cycloaddition

Li Cheng Yang; Zi Qiang Rong; Ya Nong Wang; Zher Yin Tan; Min Wang; Yu Zhao

doi:10.1002/anie.201611474

Construction of Nine-Membered Heterocycles through Palladium-Catalyzed Formal [5+4] Cycloaddition

Li Cheng Yang
, Zi Qiang Rong
, Ya Nong Wang
, Zher Yin Tan
, Min Wang
, Yu Zhao (Lead / Corresponding author)

Biological Chemistry and Drug Discovery

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

271 Citations (Scopus)

Abstract

The first catalytic formal [5+4] cycloaddition to prepare nine-membered heterocycles is presented. Under palladium catalysis, the reaction of N-tosyl azadienes and substituted vinylethylene carbonates (VECs) proceeds smoothly to produce benzofuran-fused heterocycles in uniformly high efficiency. Highly diastereoselective functionalization of the nine-membered heterocycles through peripheral attack is also demonstrated.

Original language	English
Pages (from-to)	2927-2931
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	56
Issue number	11
Early online date	6 Feb 2017
DOIs	https://doi.org/10.1002/anie.201611474
Publication status	Published - 6 Mar 2017

Keywords

heterocycles
homogeneous catalysis
nine-membered rings
palladium
[5+4] cycloaddition

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/anie.201611474

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title = "Construction of Nine-Membered Heterocycles through Palladium-Catalyzed Formal [5+4] Cycloaddition",

abstract = "The first catalytic formal [5+4] cycloaddition to prepare nine-membered heterocycles is presented. Under palladium catalysis, the reaction of N-tosyl azadienes and substituted vinylethylene carbonates (VECs) proceeds smoothly to produce benzofuran-fused heterocycles in uniformly high efficiency. Highly diastereoselective functionalization of the nine-membered heterocycles through peripheral attack is also demonstrated.",

keywords = "heterocycles, homogeneous catalysis, nine-membered rings, palladium, [5+4] cycloaddition",

author = "Yang, \{Li Cheng\} and Rong, \{Zi Qiang\} and Wang, \{Ya Nong\} and Tan, \{Zher Yin\} and Min Wang and Yu Zhao",

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T1 - Construction of Nine-Membered Heterocycles through Palladium-Catalyzed Formal [5+4] Cycloaddition

AU - Yang, Li Cheng

AU - Rong, Zi Qiang

AU - Wang, Ya Nong

AU - Tan, Zher Yin

AU - Wang, Min

AU - Zhao, Yu

PY - 2017/3/6

Y1 - 2017/3/6

N2 - The first catalytic formal [5+4] cycloaddition to prepare nine-membered heterocycles is presented. Under palladium catalysis, the reaction of N-tosyl azadienes and substituted vinylethylene carbonates (VECs) proceeds smoothly to produce benzofuran-fused heterocycles in uniformly high efficiency. Highly diastereoselective functionalization of the nine-membered heterocycles through peripheral attack is also demonstrated.

AB - The first catalytic formal [5+4] cycloaddition to prepare nine-membered heterocycles is presented. Under palladium catalysis, the reaction of N-tosyl azadienes and substituted vinylethylene carbonates (VECs) proceeds smoothly to produce benzofuran-fused heterocycles in uniformly high efficiency. Highly diastereoselective functionalization of the nine-membered heterocycles through peripheral attack is also demonstrated.

KW - heterocycles

KW - homogeneous catalysis

KW - nine-membered rings

KW - palladium

KW - [5+4] cycloaddition

UR - https://www.scopus.com/pages/publications/85012008918

U2 - 10.1002/anie.201611474

DO - 10.1002/anie.201611474

M3 - Article

C2 - 28165185

AN - SCOPUS:85012008918

SN - 1433-7851

VL - 56

SP - 2927

EP - 2931

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 11

ER -

Construction of Nine-Membered Heterocycles through Palladium-Catalyzed Formal [5+4] Cycloaddition

Abstract

Keywords

ASJC Scopus subject areas

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