Issue 31, 2008
From the journal:

Chemical Communications

meso-Phbox-Pd(ii) catalyzed tandem carbonylative cyclization of 1-ethynyl-1-propargyl acetate†

Keisuke Kato,*a   Ryuhei Teraguchi,a   Satoshi Motodate,a   Akira Uchida,c   Tomoyuki Mochida,b   Tat’yana A. Peganova,d   Nikolai V. Vologdind  and  Hiroyuki Akita*a  

* Corresponding authors

a Faculty of Pharmaceutical Sciences, Toho University, 2-2-1 Miyama, Funabashi, Chiba, Japan
E-mail: kkk@phar.toho-u.ac.jp
Fax: (+81)474-721-825
Tel: (+81)474-721-825

b Department of Chemistry, Faculty of Science, Kobe University, Rokkodai, Nada, Kobe, Japan

c Department of Chemistry, Faculty of Science, Toho University, 2-2-1 Miyama, Funabashi, Chiba, Japan

d A.N. Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences, Vavilov St.28, Moscow, Russia

Abstract

Palladium(II) catalyzed carbonylation of 1-ethynyl-1-propargyl acetate 1 is described; in the absence of the bisoxazoline (box) ligand, the second triple bond did not react, affording cyclic orthoesters 3 and 4. The use of meso-Phbox-Pd(II) strikingly changed the course of the reaction, yielding bicyclic lactone 2 by tandem carbonylative cyclization as a result of insertion of the second triple bond.

Graphical abstract: meso-Phbox-Pd(ii) catalyzed tandem carbonylative cyclization of 1-ethynyl-1-propargyl acetate

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Article information

DOI
https://doi.org/10.1039/B806207B
Article type
Communication
Submitted
11 Apr 2008
Accepted
14 May 2008
First published
23 Jun 2008

Chem. Commun., 2008, 3687-3689

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meso-Phbox-Pd(II) catalyzed tandem carbonylative cyclization of 1-ethynyl-1-propargyl acetate

K. Kato, R. Teraguchi, S. Motodate, A. Uchida, T. Mochida, T. A. Peganova, N. V. Vologdin and H. Akita, Chem. Commun., 2008, 3687 DOI: 10.1039/B806207B

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