Issue 38, 2017

Enantioselective aminocatalytic synthesis of tetrahydropyrano[2,3-c]pyrazoles via a domino Michael-hemiacetalization reaction with alkylidene pyrazolones

Abstract

An enantioselective organocatalytic domino Michael-hemiacetalization reaction between alkylidene pyrazolones and cyclic ketones/pentanal has been revealed. The fused tetrahydropyranopyrazole products having three contiguous stereocentres were obtained with perfect diastereoselectivities and in moderate to good yields with good to high enantioselectivities. Also, few synthetic transformations of the product including the formation of a spiro derivative have been demonstrated.

Graphical abstract: Enantioselective aminocatalytic synthesis of tetrahydropyrano[2,3-c]pyrazoles via a domino Michael-hemiacetalization reaction with alkylidene pyrazolones

Supplementary files

Article information

Article type
Communication
Submitted
30 Aug 2017
Accepted
13 Sep 2017
First published
13 Sep 2017

Org. Biomol. Chem., 2017,15, 8032-8036

Enantioselective aminocatalytic synthesis of tetrahydropyrano[2,3-c]pyrazoles via a domino Michael-hemiacetalization reaction with alkylidene pyrazolones

R. Maity and S. C. Pan, Org. Biomol. Chem., 2017, 15, 8032 DOI: 10.1039/C7OB02170D

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