Convenient asymmetric synthesis of both enantiomers of 3,4-disubstituted 3,4-dihydro-1,4-benzoxazin-2-ones

Author:

Youk Eunjee1,Park Wongi1,Park Yong Sun1ORCID

Affiliation:

1. Department of Chemistry, Konkuk University, Seoul, Korea

Funder

National Research Foundation of Korea

Konkuk University’s research support program for its faculty

Publisher

Informa UK Limited

Subject

Organic Chemistry

Reference8 articles.

1. For selected reviews about diverse biological activities of dihydrobenzoxazinones, see: (a) Macías, F. A.; Marín, D.; Oliveros-Bastidasab, A.; Molinillo, J. M. G. Nat. Prod. Rep. 2009, 26, 478–489. (b) Ilaš, J.; Anderluh, P. Š.; Dolenc, M. S.; Kikelj, D. Tetrahedron 2005, 61, 7325–7348. (c) Osbourn, A. E.; Lanzotti, V. Plant-Derived Natural Products: Synthesis, Function, and Application; Springer: Heidelberg, 2009. (d) Holsworth, D.; Park, W., U.S. Patent 2009311318 (A1), Substituted (S)-benzoxazinones, Dec. 17, 2009; (e) Su, S.S. Michael, Pyruvate kinase Activators for Use for Increasing Lifetime of the Red Blood Cells and Treating Anemia Patent WO 2012151440, Nov. 8, 2012. (f) Yoon, G.; Jeong, H. J.; Kim, J. J.; Cheon, S. H. Arch. Pharm. Res. 2008, 31, 989–994.

2. Relay Iron/Chiral Brønsted Acid Catalysis: Enantioselective Hydrogenation of Benzoxazinones

3. Dynamic kinetic resolution of α-chloro esters in asymmetric nucleophilic substitution using diacetone-D-glucose as a chiral auxiliary

4. Stereoselective SN2 Reactions of the (R)-Pantolactone Ester of Racemic .alpha.-Halo Carboxylic Acids with Aryl Oxides. A Synthesis of (S)-2-Aryloxy and (S)-2-Hydroxy Acids

5. In references 3 and 4, it was established that (αS)-products were provided in the substitution of both 1 and 2 with various amine nucleophiles. The absolute configuration of 3–14 is assigned by analogy. The S configuration of (S)-3 was confirmed after the conversion to 8 using H2 with Pd/C, by the comparison of chiral stationary phase-HPLC retention times and elution order with the reported values of 8 in ref. 2. ref. 2a-d.

Cited by 5 articles. 订阅此论文施引文献 订阅此论文施引文献,注册后可以免费订阅5篇论文的施引文献,订阅后可以查看论文全部施引文献

同舟云学术

1.学者识别学者识别

2.学术分析学术分析

3.人才评估人才评估

"同舟云学术"是以全球学者为主线,采集、加工和组织学术论文而形成的新型学术文献查询和分析系统,可以对全球学者进行文献检索和人才价值评估。用户可以通过关注某些学科领域的顶尖人物而持续追踪该领域的学科进展和研究前沿。经过近期的数据扩容,当前同舟云学术共收录了国内外主流学术期刊6万余种,收集的期刊论文及会议论文总量共计约1.5亿篇,并以每天添加12000余篇中外论文的速度递增。我们也可以为用户提供个性化、定制化的学者数据。欢迎来电咨询!咨询电话:010-8811{复制后删除}0370

www.globalauthorid.com

TOP

Copyright © 2019-2024 北京同舟云网络信息技术有限公司
京公网安备11010802033243号  京ICP备18003416号-3