Issue 12, 2013
From the journal:

Chemical Science

Enantioselective [3 + 2] annulation via C–H activation between cyclic N-acyl ketimines and 1,3-dienes catalyzed by iridium/chiral diene complexes†

Takahiro Nishimura,*a   Midori Nagamoto,a   Yusuke Ebea  and  Tamio Hayashibc  

* Corresponding authors

a Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan
E-mail: tnishi@kuchem.kyoto-u.ac.jp
Fax: +81 75 753 3988
Tel: +81 75 753 3987

b Institute of Materials Research and Engineering, A*STAR, 3 Research Link, Singapore 117602

c Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543

Abstract

Enantioselective [3 + 2] annulation between 1,3-dienes and N-acyl ketimines in situ generated from 3-aryl-3-hydroxyisoindolin-1-ones proceeded via C–H activation to give spiroaminoindane derivatives in high yields with high regio- and enantioselectivity, which is realized by use of an Ir/chiral diene catalyst.

Graphical abstract: Enantioselective [3 + 2] annulation via C–H activation between cyclic N-acyl ketimines and 1,3-dienes catalyzed by iridium/chiral diene complexes

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Article information

DOI
https://doi.org/10.1039/C3SC52379A
Article type
Edge Article
Submitted
26 Aug 2013
Accepted
20 Sep 2013
First published
23 Sep 2013

Chem. Sci., 2013,4, 4499-4504

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Enantioselective [3 + 2] annulation via C–H activation between cyclic N-acyl ketimines and 1,3-dienes catalyzed by iridium/chiral diene complexes

T. Nishimura, M. Nagamoto, Y. Ebe and T. Hayashi, Chem. Sci., 2013, 4, 4499 DOI: 10.1039/C3SC52379A

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