Abstract
A series of hydrogen bonding organocatalysts was synthesized from dianhydrohexitol and was used for the first time in organocatalysis for Friedel-Crafts alkylation of indoles with nitroalkenes. Moderate yields and enantioselectivities were achieved.
Highlights
The use of small and metal-free homochiral organic molecules to catalyze enantioselective transformation, named organocatalysis, is a fascinating research area in asymmetric synthesis
We report our preliminary results concerning the design and the synthesis of new chiral thioureas derived from isoidide and isomannide and their evaluation as organocatalysts in enantioselective Friedel-Crafts alkylation of indoles with nitroalkenes.[31,32,33,34,35,36,37,38,39,40,41]
The synthesis of diamine 944 was initiated by the ditosylation of the hydroxyl groups of isomannide in the presence of a catalytic amount of DMAP leading to 7 in 91% yield
Summary
The use of small and metal-free homochiral organic molecules to catalyze enantioselective transformation, named organocatalysis, is a fascinating research area in asymmetric synthesis.
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