Issue 10, 2015

Enantioselective assembly of functionalized carbocyclic spirooxindoles using an l-proline derived thiourea organocatalyst

Abstract

Sequential vinylogous Michael addition–cyclization reactions of vinyl malononitriles with isatylidene malononitrile were accomplished using L-proline derived bifunctional thiourea. Cyclohexylidine malononitrile afforded exclusively the single diastereomer with good to excellent enantioselectivity (up to 99% ee) for diverse oxindole spirocyclohexene derivatives. Tetralone derived α,α-dicyano alkene was also employed to access spirocyclic oxindole scaffolds with an excellent level of stereoselectivity (up to 99% ee).

Graphical abstract: Enantioselective assembly of functionalized carbocyclic spirooxindoles using an l-proline derived thiourea organocatalyst

Supplementary files

Article information

Article type
Paper
Submitted
03 Nov 2014
Accepted
19 Dec 2014
First published
19 Dec 2014

RSC Adv., 2015,5, 7370-7379

Enantioselective assembly of functionalized carbocyclic spirooxindoles using an L-proline derived thiourea organocatalyst

V. P. Reddy Gajulapalli, P. Vinayagam and V. Kesavan, RSC Adv., 2015, 5, 7370 DOI: 10.1039/C4RA13711F

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