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

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. Ad...

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Bibliographic Details
Published in:Journal of organic chemistry 2023-12, Vol.88 (23), p.16666-16670
Main Authors: Hart, Alison P., DeGraw, Caroline J., Rustin, Gavin J., Donahue, Matthew G., Pigza, Julie A.
Format: Article
Language:English
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c01838