3-Carboxamide oxindoles as 1,3-C,N-bisnucleophiles for the highly diastereoselective synthesis of CF3-containing spiro-δ-lactam oxindoles featuring acyl at the ortho-position of spiro carbon atom

A simple and efficient strategy has been established for the synthesis of delta-lactam fused oxindoles via the Michael/N-hemiketalization cascade reaction of 3-carboxamide oxindoles and alpha,beta-unsaturated trifluoromethyl ketones. A wide range of structurally novel CF3-containing spiro-delta-lactam oxindoles featuring acyl at the ortho-position of spiro carbon atoms were obtained in moderate to good yields with excellent diastereoselectivities under mild conditions. This work represents the first example of a systematic study of 3-carboxamide oxindoles as 1,3-C,N bisnucleophiles. (C) 2021 Elsevier Ltd. All rights reserved.

Automated summary

A range of structurally novel CF3-containing spiro-delta-lactam oxindoles were successfully synthesized via the Michael/N-hemiketalization cascade reaction, with moderate to good yields and excellent diastereoselectivities. This work represents the first systematic study of 3-carboxamide oxindoles as 1,3-C,N bisnucleophiles.