Issue 87, 2015
From the journal:

RSC Advances

Recyclable organocatalyst-promoted one-pot Michael/aza-Henry/lactamization reactions for fluorinated 2-piperidinones bearing four stereogenic centres†

Xin Huang,a   Kenny Pham,a   Xiaofeng Zhang,a   Wen-Bin Yi,b   Jeremy H. Hyatt,a   Anthony P. Tran,a   Jerry P. Jasinskic  and  Wei Zhang*a  

* Corresponding authors

a Department of Chemistry, University of Massachusetts Boston, 100 Morrissey Boulevard, Boston, MA 02125, USA
E-mail: wei2.zhang@umb.edu

b School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094, China

c Department of Chemistry, Keene State College, Keene, NH 03435-2001, USA

Abstract

A one-pot Michael/aza-Henry/lactamization reaction promoted by recyclable fluorous bifunctional cinchona alkaloid/thiourea organocatalyst has been developed for asymmetric synthesis of fluorine-containing 2-piperidinones bearing four stereogenic centers. The asymmetric Michael adducts induce the formation of other three stereogenic centers to afford products with up to 99% ee and 15 : 1 dr.

Graphical abstract: Recyclable organocatalyst-promoted one-pot Michael/aza-Henry/lactamization reactions for fluorinated 2-piperidinones bearing four stereogenic centres

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Article information

DOI
https://doi.org/10.1039/C5RA15306A
Article type
Communication
Submitted
31 Jul 2015
Accepted
13 Aug 2015
First published
13 Aug 2015

RSC Adv., 2015,5, 71071-71075

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Recyclable organocatalyst-promoted one-pot Michael/aza-Henry/lactamization reactions for fluorinated 2-piperidinones bearing four stereogenic centres

X. Huang, K. Pham, X. Zhang, W. Yi, J. H. Hyatt, A. P. Tran, J. P. Jasinski and W. Zhang, RSC Adv., 2015, 5, 71071 DOI: 10.1039/C5RA15306A

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