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Cu-Catalyzed Regio- and Diastereoselective Propargylic Substitution of N-Hydroxyphthalimide Esters: Access to
Xinkun Wang1, Peisen Yu2, Yu Zhou3
1School of Food Science and Chemical Engineering, Hubei University of Arts and Science, Xiangyang441053, P. R. China.
Abstract:
Herein, we report the copper-catalyzed propargylic substitution reaction between N-acyl phenylglycine N-hydroxyphthalimide (NHP) esters as a direct C-2-position nucleophile to racemic propargylic carbonates. The reaction affords multifunctionalized N,O-acetal products bearing a terminal-alkyne unit in high yields (up to 97%) with excellent diastereoselectivities (up to >19:1 dr) under mild reaction conditions. Moreover, the products serve as versatile intermediates that can be readily transformed into structurally diverse derivatives, offering significant potential for the exploitation of pharmaceutically relevant molecules.
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