Ortho metalation directed by. alpha.-amino alkoxides

DL Comins, JD Brown

Index: Comins, Daniel L.; Brown, Jack D. Journal of Organic Chemistry, 1984 , vol. 49, # 6 p. 1078 - 1083

Full Text: HTML

Citation Number: 161

Abstract

The addition of aromatic aldehydes to certain lithium dialkylamides in benzene or tetrahydrofuran gave a-amino alkoxides which were ortho lithiated with excess n- butyllithium. Subsequent alkylation and hydrolysis provided ortho-substituted aromatic aldehydes via a one-pot reaction. The ortho metalation of a-amino alkoxides derived from 1- and 2-naphthaldehyde and various substituted benzaldehydes was examined. When N, ...