Palladium-catalyzed oxidative 6-exo-trig cyclization of 1,6-enynes: facile synthesis of bicyclo[4.1.0]heptan-5-ones

Bang Liu; Ren-Jie Song; Xuan-Hui Ouyang; Yang Li; Ming Hu; Jin-Heng Li

doi:10.1039/C5CC04300J

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Palladium-catalyzed oxidative 6-exo-trig cyclization of 1,6-enynes: facile synthesis of bicyclo[4.1.0]heptan-5-ones†

Bang Liu,^a Ren-Jie Song,*^a Xuan-Hui Ouyang,^a Yang Li,^a Ming Hu^a and Jin-Heng Li*^ab

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* Corresponding authors

^a State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, China
E-mail: srj0731@hnu.edu.cn, jhli@hnu.edu.cn

^b State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China

Abstract

We here describe a new palladium-catalyzed oxidative 6-exo-trig cyclization of 1,6-enynes at room temperature using tBuONO as an oxidant for the synthesis of 3-bicyclo[4.1.0]heptan-5-ones. This cascade strategy involves the hydration, cyclization and cyclopropanation sequence, and represents a new transition-metal-catalyzed oxidative cyclization of 1,6-enynes in a 6-exo-trig fashion.

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DOI: https://doi.org/10.1039/C5CC04300J
Article type: Communication
Submitted: 26 May 2015
Accepted: 30 Jun 2015
First published: 06 Jul 2015

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Chem. Commun., 2015,51, 12819-12822

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Palladium-catalyzed oxidative 6-exo-trig cyclization of 1,6-enynes: facile synthesis of bicyclo[4.1.0]heptan-5-ones

B. Liu, R. Song, X. Ouyang, Y. Li, M. Hu and J. Li, Chem. Commun., 2015, 51, 12819 DOI: 10.1039/C5CC04300J

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Chemical Communications

Palladium-catalyzed oxidative 6-exo-trig cyclization of 1,6-enynes: facile synthesis of bicyclo[4.1.0]heptan-5-ones†

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Palladium-catalyzed oxidative 6-exo-trig cyclization of 1,6-enynes: facile synthesis of bicyclo[4.1.0]heptan-5-ones

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