PPh3-catalyzed synthesis of dicyano-2-methylenebut-3-enoates as efficient dienes in catalytic asymmetric inverse-electron-demand Diels–Alder reaction

Xianxing Jiang; Dan Fu; Xiaomei Shi; Shoulei Wang; Rui Wang

doi:10.1039/C1CC12834E

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PPh₃-catalyzed synthesis of dicyano-2-methylenebut-3-enoates as efficient dienes in catalytic asymmetric inverse-electron-demand Diels–Alder reaction†

Xianxing Jiang,^ab Dan Fu,^a Xiaomei Shi,^a Shoulei Wang^a and Rui Wang*^ab

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* Corresponding authors

^a State Key Laboratory of Applied Organic Chemistry, Institute of Biochemistry and Molecular Biology, Key Laboratory of Preclinical Study for New Drugs of Gansu Province, Lanzhou University, Lanzhou 730000, China
E-mail: wangrui@lzu.edu.cn
Fax: (+86)-931-8911255

^b State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, China
E-mail: wangrui@lzu.edu.cn

Abstract

We present here the synthesis of dicyano-2-methylenebut-3-enoates as novel Diels–Alder dienes through an efficient PPh₃-catalyzed strategy, and an unprecedented PPh₃-catalyzed addition/all-carbon-based asymmetric inverse-electron-demand Diels–Alder sequence reaction is disclosed for the first time.

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Article information

DOI: https://doi.org/10.1039/C1CC12834E
Article type: Communication
Submitted: 14 May 2011
Accepted: 31 May 2011
First published: 21 Jun 2011

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Chem. Commun., 2011,47, 8289-8291

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PPh₃-catalyzed synthesis of dicyano-2-methylenebut-3-enoates as efficient dienes in catalytic asymmetric inverse-electron-demand Diels–Alder reaction

X. Jiang, D. Fu, X. Shi, S. Wang and R. Wang, Chem. Commun., 2011, 47, 8289 DOI: 10.1039/C1CC12834E

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