Published in
American Chemical Society, Journal of Organic Chemistry, 22(73), p. 9151-9154, 2008
DOI: 10.1021/jo801867w
Links
- ORCID
- American Chemical Society
- [www.ncbi.nlm.nih.gov] | PDF
- [www.researchgate.net] | PDF
- [www.ncbi.nlm.nih.gov] | PDF
- [www.ncbi.nlm.nih.gov] | PDF
- [europepmc.org] | PDF
Tools
A Versatile Synthesis of Unsymmetrical 3,3′-Bioxindoles: Stereoselective Mukaiyama Aldol Reactions of 2-Siloxyindoles with Isatins
Journal article published in 2008 by
J. Michael Ellis 
,
Larry E. Overman,
Huw R. Tanner,
Jocelyn Wang
,
Larry E. Overman,
Huw R. Tanner,
Jocelyn Wang
This paper is available in a repository.
Full text: Download
Preprint: archiving allowed
- Must obtain written permission from Editor
- Must not violate ACS ethical Guidelines
Postprint:
archiving restricted
- Must obtain written permission from Editor
- Must not violate ACS ethical Guidelines
Published version:
archiving forbidden
Data provided by 
Abstract
A new synthesis of 3,3'-bioxindoles is reported that is well suited for the preparation of unsymmetrical structures. In the key step, 3-hydroxy-3,3'-bioxindoles are constructed by Mukaiyama aldol reaction of 2-siloxyindoles with isatins. These tertiary carbinols are formed in high diastereoselectivities, with substitution at various positions of the isatin and the 2-siloxyindole being tolerated.