Issue 9, 2004
From the journal:

Organic & Biomolecular Chemistry

Synthesis of benzo-fused lactams and lactonesvia Ru(ii)-catalyzed cycloaddition of amide- and ester-tethered α,ω-diynes with terminal alkynes: electronic directing effect of internal conjugated carbonyl group

Yoshihiko Yamamoto,*a   Keisuke Kinpara,a   Tomoaki Saigoku,a   Hisao Nishiyamaa  and  Kenji Itohb  

* Corresponding authors

a Department of Applied Chemistry, Department of Molecular Design and Engineering, Graduate School of Engineering, Nagoya University, Chikusa, Nagoya 464-8603, Japan
E-mail: yamamoto@apchem.nagoya-u.ac.jp
Fax: 81 52 789 3209
Tel: 81 52 789 3337

b Department of Molecular Design and Engineering, Graduate School of Engineering, Nagoya University, Chikusa, Nagoya 464-8603, Japan
Fax: 81 52 789 3209
Tel: 81 52 789 3337

Abstract

In the presence of a catalytic amount of Cp*RuCl(cod), 1,6- and 1,7-diynes connected by an amide or an ester tether underwent cycloaddition with terminal alkynes at room temperature to give rise to cycloadducts in 40–93% yields with 63 : 37–83 : 17 regioisomer ratios.

Graphical abstract: Synthesis of benzo-fused lactams and lactones via Ru(ii)-catalyzed cycloaddition of amide- and ester-tethered α,ω-diynes with terminal alkynes: electronic directing effect of internal conjugated carbonyl group

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Article information

DOI
https://doi.org/10.1039/B402649G
Article type
Paper
Submitted
23 Feb 2004
Accepted
11 Mar 2004
First published
07 Apr 2004

Org. Biomol. Chem., 2004,2, 1287-1294

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Synthesis of benzo-fused lactams and lactones via Ru(II)-catalyzed cycloaddition of amide- and ester-tethered α,ω-diynes with terminal alkynes: electronic directing effect of internal conjugated carbonyl group

Y. Yamamoto, K. Kinpara, T. Saigoku, H. Nishiyama and K. Itoh, Org. Biomol. Chem., 2004, 2, 1287 DOI: 10.1039/B402649G

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