Journal
ORGANIC LETTERS
Volume 23, Issue 13, Pages 5076-5080Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c01607
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This study introduces an enantioselective oxidative cyclization method for N-allyl carboxamides using a chiral triazole-substituted iodoarene catalyst, yielding highly enantioenriched oxazolines and oxazines with up to 94% yield and 98% ee enantioselectivity. The method is versatile, allowing the construction of quaternary stereocenters and the use of various substrates beyond N-allyl amides, demonstrating the value of the chiral heterocycles as strategic intermediates for the synthesis of other enantioenriched target structures.
This study presents an enantioselective oxidative cyclization of N-allyl carboxamides via a chiral triazole-substituted iodoarene catalyst. The method allows the synthesis of highly enantioenriched oxazolines and oxazines, with yields of up to 94% and enantioselectivities of up to 98% ee. Quaternary stereocenters can be constructed and, besides N-allyl amides, the corresponding thioamides and imideamides are well tolerated as substrates, giving rise to a plethora of chiral 5-membered N-heterocycles. By applying a multitude of further functionalizations, we finally demonstrate the high value of the observed chiral heterocycles as strategic intermediates for the synthesis of other enantioenriched target structures.
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