Stereoselective Synthesis of Functionalized Benzooxazepino[5,4- a]isoindolone Derivatives via Cesium Carbonate Catalyzed Formal [5 + 2] Annulation of 2-(2-Hydroxyphenyl)isoindoline-1,3-dione with Allenoates

Chao Yao; Yishu Bao; Tao Lu; Qingfa Zhou

doi:10.1021/acs.orglett.8b00382

Stereoselective Synthesis of Functionalized Benzooxazepino[5,4- a]isoindolone Derivatives via Cesium Carbonate Catalyzed Formal [5 + 2] Annulation of 2-(2-Hydroxyphenyl)isoindoline-1,3-dione with Allenoates

Org Lett. 2018 Apr 20;20(8):2152-2155. doi: 10.1021/acs.orglett.8b00382. Epub 2018 Apr 4.

Authors

Chao Yao¹, Yishu Bao¹, Tao Lu¹, Qingfa Zhou¹

Affiliation

¹ State Key Laboratory of Natural Medicines, Department of Organic Chemistry , China Pharmaceutical University , Nanjing , 210009 , P. R. China.

PMID: 29616551
DOI: 10.1021/acs.orglett.8b00382

Abstract

In this work, we present a strategy for the stereoselective synthesis of functionalized benzooxazepino[5,4- a]isoindolone derivatives via a Cs₂CO₃-catalyzed domino β-addition and γ-aldol reaction of 2-(2-hydroxyphenyl)isoindoline-1,3-dione derivatives with allenoates, which offers an avenue for a combination of the structural unity between benzooxazepine and isoindolone motifs in synthetically useful yields with high stereoselectivities under mild conditions. Remarkably, it is the first example of highly stereoselective Cs₂CO₃-catalyzed formal [5 + 2] annulation of 2-(2-hydroxyphenyl)isoindoline-1,3-dione with allenoates.

Publication types

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