通过苯并[e]氧杂环庚烷-4-羧酸酯与手性氨基酸乙酯的统一反应来立体特异性合成 3,4-二氢-2-萘并-1,4-恶嗪-2-酮。

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

机构信息

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

出版信息

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

DOI:10.1021/acs.joc.9b02624

PMID:31995711

Abstract

A novel and efficient stereocontrolled method has been developed for the preparation of chiral 3,4-dihydro-2-naphtho[1,2-][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-2-naphtho-1,4-oxazinones have been achieved in one step by the formation of C-N, C-C, and C-O bonds.

摘要

首次发展了一种新型高效的立体控制方法，通过苯并[1,2-e][1,4]氧氮杂卓-4-羧酸酯与手性氨基酸乙酯的反应，来制备手性 3,4-二氢-2-萘并[1,2-][1,4]恶嗪-2-酮。通过形成 C-N、C-C 和 C-O 键，一步即可得到手性 3,4-二氢-2-萘并-1,4-恶嗪酮。