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Title: Co–salen complexes as catalysts for the asymmetric Henry reaction – reversed enantioselectivity through simple ligand modification

Journal Article · · RSC Advances
DOI:https://doi.org/10.1039/c4ra16931j· OSTI ID:1657177
 [1]; ORCiD logo [1]
  1. New York University, NY (United States)
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The asymmetric Henry reaction is an efficient method for the synthesis of enantioenriched nitro alcohols. Here, we investigated the catalytic activity and enantioselectivity of derivatives of Co–salen [salen = N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexane-diamine] in this reaction. Tetrahydro-salen (salan) complexes displayed a reversed enantioselectivity compared to their Schiff-base counterparts. Oligomeric Co–salen catalysts showed a higher activity than their small molecule analogues, indicating a bimetallic pathway.

Research Organization:
Georgia Institute of Technology, Atlanta, GA (United States)
Sponsoring Organization:
USDOE Office of Science (SC), Basic Energy Sciences (BES)
Contributing Organization:
New York University
Grant/Contract Number:
FG02-03ER15459
OSTI ID:
1657177
Journal Information:
RSC Advances, Vol. 5, Issue 37; ISSN 2046-2069
Publisher:
Royal Society of ChemistryCopyright Statement
Country of Publication:
United States
Language:
English
Citation Metrics:
Cited by: 16 works
Citation information provided by
Web of Science

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Cited By (5)

The influence of axial ligands on the catalytic activity and enantioselectivity of salen‐Mn complexes in the asymmetric epoxidation journal May 2019
Copper Complex of Pinene based Schiff base [CuSBADBH] 2 : Synthesis and its Application in Catalytic Asymmetric Nitroaldol (Henry) Reaction journal June 2016
Mono and Dinuclear Cu(II) Carboxylate Complexes with Pyridine and 1‐methylimidazole as Co–Ligands: Synthesis, Structure, Antibacterial Activity and Catalytic Nitroaldol Reactions journal July 2019
Structure and asymmetric epoxidation reactivity of chiral Mn( iii ) salen catalysts modified by different axial anions journal January 2015
A NbO type Cu( ii ) metal–organic framework showing efficient catalytic activity in the Friedländer and Henry reactions journal January 2017

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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY