Please use this identifier to cite or link to this item: https://doi.org/10.1002/ejoc.201001404
Title: Diarylprolinol silyl ether catalyzed asymmetric friedel-crafts alkylation of indoles with α,β-unsaturated aldehydes: Enhanced enantioselectivity and mechanistic investigations
Authors: Shi, Z.-H.
Sheng, H.
Yang, K.-F.
Jiang, J.-X.
Lai, G.-Q.
Lu, Y. 
Xu, L.-W.
Keywords: Alkylation
Asymmetric synthesis
Organocatalysis
Reaction mechanisms
Silicon
Issue Date: Jan-2011
Citation: Shi, Z.-H., Sheng, H., Yang, K.-F., Jiang, J.-X., Lai, G.-Q., Lu, Y., Xu, L.-W. (2011-01). Diarylprolinol silyl ether catalyzed asymmetric friedel-crafts alkylation of indoles with α,β-unsaturated aldehydes: Enhanced enantioselectivity and mechanistic investigations. European Journal of Organic Chemistry (1) : 66-70. ScholarBank@NUS Repository. https://doi.org/10.1002/ejoc.201001404
Abstract: A highly enantioselective Friedel-Crafts alkylation of indoles with α,β-unsaturated aldehydes with excellent enantioselectivities (up to >99%ee) has been developed, and this improved method offers substantial advantages over traditional approaches, not only by avoiding the use of acids or bases, but also in terms of the higher level of stereoselectivity. In addition, we have demonstrated through a plausible mechanism that the role of silicon in the diarylprolinol silyl ethers (Jørgensen-Hayashi organocatalyst) not only serves as a bulky group to induce steric repulsion but also serves as a Lewis acidic promoter to accelerate the reaction between the secondary amine and the substrate (α,β-unsaturated aldehyde). A highly enantioselective Friedel-Craftsalkylation of indoles with α,β-unsaturated aldehydes with excellent enantioselectivities (up to >99%ee) has been developed, and this method offers substantial advantagesover traditional approaches, not only by avoiding the use of acids or bases, but also in terms of the high level of stereoselectivity. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Source Title: European Journal of Organic Chemistry
URI: http://scholarbank.nus.edu.sg/handle/10635/75936
ISSN: 1434193X
DOI: 10.1002/ejoc.201001404
Appears in Collections:Staff Publications

Show full item record
Files in This Item:
There are no files associated with this item.

SCOPUSTM   
Citations

24
checked on Jul 13, 2018

WEB OF SCIENCETM
Citations

19
checked on Jun 13, 2018

Page view(s)

26
checked on Mar 12, 2018

Google ScholarTM

Check

Altmetric


Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.