Issue 35, 2016

Enantioselective synthesis of spiro[indoline-3,4′-pyrano[2,3-c]pyrazole] derivatives via an organocatalytic asymmetric Michael/cyclization cascade reaction

Abstract

An efficient enantioselective synthesis of spiro[indoline-3,4′-pyrano[2,3-c]pyrazole] derivatives by a cascade reaction between pyrazolones and isatylidene malononitriles is described. With only 1 mol% of (DHQD)2PYR, chiral spirooxindole derivatives have been produced in excellent yields (96–99%) with good-to-excellent enantioselectivities (up to 91% ee).

Graphical abstract: Enantioselective synthesis of spiro[indoline-3,4′-pyrano[2,3-c]pyrazole] derivatives via an organocatalytic asymmetric Michael/cyclization cascade reaction

Supplementary files

Article information

Article type
Paper
Submitted
09 Jun 2016
Accepted
06 Aug 2016
First published
09 Aug 2016

Org. Biomol. Chem., 2016,14, 8346-8355

Enantioselective synthesis of spiro[indoline-3,4′-pyrano[2,3-c]pyrazole] derivatives via an organocatalytic asymmetric Michael/cyclization cascade reaction

J. Xie, X. Xing, F. Sha, Z. Wu and X. Wu, Org. Biomol. Chem., 2016, 14, 8346 DOI: 10.1039/C6OB01256F

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements