Background: The Diels-Alder reaction is one of the important and highly applicable reactions
in the area of organic synthesis. It is useful to obtain six membered cyclic compounds using onestep
inter- or intra-molecular reaction protocol. The high degree of regio- as well as stereoselectivity
can be easily obtained by this reaction. The aim of this proposed work is to increase the efficiency of
MacMillan catalyst using ionic liquid medium to obtain the Diels-Alder reaction product in good yield
Methods: MacMillan’s catalyst was used in pyridinium based ionic liquids to promote Diels-Alder
reaction. After completion the reaction product was isolated by simple ether washing and the catalytic system was reused
for the next reaction cycle.
Results: A highly enantio- and diastereoselective Diels–Alder reaction was obtained by using MacMillan’s catalyst in
ionic liquid medium. Surprisingly, Ionic liquid mediated MacMillan’s catalyst was found highly active in term of yield
and selectivity for the Diels -Alder reaction with the added advantage of 8 times catalyst recycling. Synthesis of steroid, is
the major outcome of our developed protocol.
Conclution: MwacMillan’s catalyst was found highly active in terms of yield and selectivity. We also extended the
application of our proposed protocol and successfully synthesized the biologically active steroid.