Issue 15, 2016
From the journal:

RSC Advances

Organocatalytic construction of spirooxindole naphthoquinones through Michael/hemiketalization using l-proline derived bifunctional thiourea†

V. Pratap Reddy Gajulapalli,a   Kanduru Lokesh,a   Manjunatha Vishwanatha  and  Venkitasamy Kesavan*a  

* Corresponding authors

a Chemical Biology Laboratory, Department of Biotechnology, Bhupat and Jyothi Mehtha School of Biosciences, Indian Institute of Technology Madras, Chennai-600036, India
E-mail: vkesavan@iitm.ac.in
Fax: +91-44-2257-4102
Tel: +91-44-2257-4124

Abstract

Michael/hemiketalization of 2-hydroxy-1,4-naphthoquinone to oxindole ketoester was studied using a series of chiral bifunctional organocatalysts. Good yields (up to 91%) and excellent enantioselectivities (up to 98%) were achieved by using a proline derived thiourea catalyst. This method provides an elegant synthetic route to access oxindole containing naphthoquinone derivatives.

Graphical abstract: Organocatalytic construction of spirooxindole naphthoquinones through Michael/hemiketalization using l-proline derived bifunctional thiourea

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Article information

DOI
https://doi.org/10.1039/C5RA25025K
Article type
Communication
Submitted
25 Nov 2015
Accepted
14 Jan 2016
First published
22 Jan 2016

RSC Adv., 2016,6, 12180-12184

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Organocatalytic construction of spirooxindole naphthoquinones through Michael/hemiketalization using L-proline derived bifunctional thiourea

V. Pratap Reddy Gajulapalli, K. Lokesh, M. Vishwanath and V. Kesavan, RSC Adv., 2016, 6, 12180 DOI: 10.1039/C5RA25025K

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