Issue 35, 2013
From the journal:

Organic & Biomolecular Chemistry

Pd(ii)–SDP-catalyzed enantioselective 5-exo-digcyclization of γ-alkynoic acids: application to the synthesis of functionalized dihydofuran-2(3H)-ones containing a chiral quaternary carbon center†

Vellaisamy Sridharan,*ab   Lulu Fan,a   Shinobu Takizawa,a   Takeyuki Suzukia  and  Hiroaki Sasai*a  

* Corresponding authors

a The Institute of Scientific and Industrial Research (ISIR), Osaka University, Mihogaoka, Ibaraki-shi, Osaka 567-0047, Japan
E-mail: sasai@sanken.osaka-u.ac.jp
Fax: +81 6 6879 8465
Tel: +81 6 6879 8469

b Department of Chemistry, School of Chemical and Biotechnology, SASTRA University, Thanjavur – 613 401, Tamil Nadu, India
E-mail: vsridharan@scbt.sastra.edu, vesridharan@gmail.com

Abstract

The Pd(II)–SDP-catalyzed first enantioselective intramolecular cyclization of α,α-disubstituted γ-alkynoic acids is described. This 5-exo-dig cyclization afforded dihydrofuran-2(3H)-ones bearing a chiral quaternary carbon center in excellent yields with enantioselectivities up to 71%. A mechanism involving palladium(II) species is proposed to rationalize the outcome of the reaction.

Graphical abstract: Pd(ii)–SDP-catalyzed enantioselective 5-exo-dig cyclization of γ-alkynoic acids: application to the synthesis of functionalized dihydofuran-2(3H)-ones containing a chiral quaternary carbon center

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Article information

DOI
https://doi.org/10.1039/C3OB41103F
Article type
Paper
Submitted
27 May 2013
Accepted
17 Jul 2013
First published
17 Jul 2013

Org. Biomol. Chem., 2013,11, 5936-5943

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Pd(II)–SDP-catalyzed enantioselective 5-exo-dig cyclization of γ-alkynoic acids: application to the synthesis of functionalized dihydofuran-2(3H)-ones containing a chiral quaternary carbon center

V. Sridharan, L. Fan, S. Takizawa, T. Suzuki and H. Sasai, Org. Biomol. Chem., 2013, 11, 5936 DOI: 10.1039/C3OB41103F

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