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Efficient catalyst for tandem solvent free enantioselective Knoevenagel-formal [3+3] cycloaddition and Knoevenagel-hetero-Diels-Alder reactions

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Title Efficient catalyst for tandem solvent free enantioselective Knoevenagel-formal [3+3] cycloaddition and Knoevenagel-hetero-Diels-Alder reactions
 
Creator FERNANDES, S
RAJAKANNU, P
BHAT, SV
 
Subject ONE-POT SYNTHESIS
ASYMMETRIC ADDITION
COLEUS-FORSKOHLII
ALDEHYDES
PYRANOQUINOLINONES
TITANIUM
LABDANE
 
Description In this study a highly efficient catalyst has been observed for tandem solvent free enantioselective Knoevenagel-formal [3+3] cycloaddition and Knoevenagel-hetero-Diels-Alder reactions. Thus, the synthesis of bicyclic tetrahydro-2H-chromen-5(6H)-one and tricyclic octahydro-2H-benzo[c]-chromen-1(6H)-one derivatives with enantioselectivity up to ee 99% has been achieved in the presence of a chiral Lewis acid assisted Bronsted acid (LBA), titanium-isopropoxy-(S)-BINOLate under solvent free conditions. The stereochemistry of the tricyclic product 10 has been further supported by single crystal X-ray analysis. This domino powerful strategy combines both the economic and environmental aspects of organic chemistry, which are necessary for academic and industrial applications.
 
Publisher ROYAL SOC CHEMISTRY
 
Date 2016-01-15T07:23:43Z
2016-01-15T07:23:43Z
2015
 
Type Article
 
Identifier RSC ADVANCES, 5(83)67706-67711
2046-2069
http://dx.doi.org/10.1039/c5ra09865c
http://dspace.library.iitb.ac.in/jspui/handle/100/18041
 
Language en