Squaramide Organocatalyzed Addition of a Masked Acyl Cyanide to β-Nitrostyrenes

Authors

Alison P. Hart, University of Southern MississippiFollow
Caroline J. DeGraw, University of Southern Mississippi
Gavin J. Rustin, University of Southern MississippiFollow
Matthew G. Donahue, University of Southern MississippiFollow
Julie A. Pigza, University of Southern MississippiFollow

Document Type

Article

Publication Date

11-15-2023

School

Mathematics and Natural Sciences

Abstract

A method for the squaramide-organocatalyzed enantioselective addition of a silyl-protected masked acyl cyanide (MAC) reagent to various β-nitrostyrenes is described. Reactions are carried out in a freezer and provide products cleanly and in high enantioselectivities at very low catalyst loadings. Adducts are then unmasked, providing various oxidation state 3 functional groups, thereby highlighting the utility of these MAC reagents and a new strategy for the preparation of β-amino acids.

Volume

88

Issue

23

First Page

16666

Last Page

16670

Recommended Citation

Hart, A. P., DeGraw, C. J., Rustin, G. J., Donahue, M. G., Pigza, J. A. (2023). Squaramide Organocatalyzed Addition of a Masked Acyl Cyanide to β-Nitrostyrenes. , 88(23), 16666-16670.
Available at: https://aquila.usm.edu/fac_pubs/21752