Next Article in Journal
Dendrimers Containing Ferrocene and Porphyrin Moieties: Synthesis and Cubic Non-Linear Optical Behavior
Next Article in Special Issue
A General and Simple Diastereoselective Reduction by L-Selectride: Efficient Synthesis of Protected (4S,5S)-Dihydroxy Amides
Previous Article in Journal
Synthesis, Antimicrobial, and Anti-inflammatory Activities of Novel 5-(1-Adamantyl)-4-arylideneamino-3-mercapto-1,2,4-triazoles and Related Derivatives
Previous Article in Special Issue
Synthesis and Conformational Study of a Novel Macrocyclic Chiral(Salen) ligand and its Uranyl and Mn Complexes
Molecules 2010, 15(4), 2551-2563; doi:10.3390/molecules15042551
Article

Organocatalytic Michael Addition of 1,3-Dicarbonyl Indane Compounds to Nitrostyrenes

, , , , , *,  and *
Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Hangzhou 310012, China
* Authors to whom correspondence should be addressed.
Received: 9 December 2009 / Revised: 3 March 2010 / Accepted: 19 March 2010 / Published: 12 April 2010
(This article belongs to the Special Issue Asymmetric Synthesis)
Download PDF [315 KB, uploaded 18 June 2014]   |  

Abstract

To map out the efficient organocatalyst requirements in the Michael addition of 1,3-dicarbonyl indane compounds to nitrostyrenes, a dozen different amino organocatalysts containing a p-toluenesulfonyl group (Ts) have been evaluated; excellent enantio-selectivities (up to er 92:8) were obtained with a primary amine-based Ts-DPEN catalyst and a plausible catalytic reaction mechanism was proposed on the basis of the experimental results.
Keywords: organocatalysis; Michael reaction; primary amine; diamine organocatalysis; Michael reaction; primary amine; diamine
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
SciFeed

Share & Cite This Article

Further Mendeley | CiteULike
Export to BibTeX |
EndNote |
RIS
MDPI and ACS Style

Jiang, Z.-Y.; Yang, H.-M.; Ju, Y.-D.; Li, L.; Luo, M.-X.; Lai, G.-Q.; Jiang, J.-X.; Xu, L.-W. Organocatalytic Michael Addition of 1,3-Dicarbonyl Indane Compounds to Nitrostyrenes. Molecules 2010, 15, 2551-2563.

View more citation formats

Related Articles

Article Metrics

For more information on the journal, click here

Comments

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert