Stereospecific Synthesis of 3,4-Dihydro-2 H-naphtho-1,4-oxazin-2-ones by Unification of Benzoxepine-4-carboxylates with Chiral Amino Acid Ethyl Esters

Veera Prasad Kasagani; Siva Hariprasad Kurma; China Raju Bhimapaka

doi:10.1021/acs.joc.9b02624

Stereospecific Synthesis of 3,4-Dihydro-2 H-naphtho-1,4-oxazin-2-ones by Unification of Benzoxepine-4-carboxylates with Chiral Amino Acid Ethyl Esters

J Org Chem. 2020 Mar 6;85(5):2976-2983. doi: 10.1021/acs.joc.9b02624. Epub 2020 Feb 12.

Authors

Veera Prasad Kasagani¹, Siva Hariprasad Kurma¹, China Raju Bhimapaka¹

Affiliation

¹ Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad-500007, India.

PMID: 31995711
DOI: 10.1021/acs.joc.9b02624

Abstract

A novel and efficient stereocontrolled method has been developed for the preparation of chiral 3,4-dihydro-2H-naphtho[1,2-b][1,4]oxazin-2-ones by the reaction of benzoxepine-4-carboxylates with chiral amino acid ethyl esters for the first time. The chiral 3,4-dihydro-2H-naphtho-1,4-oxazinones have been achieved in one step by the formation of C-N, C-C, and C-O bonds.

Publication types

Research Support, Non-U.S. Gov't