Aromatization-driven cascade [1,5]-hydride transfer/cyclization for synthesis of spirochromanes

被引：9
作者：
Cao, Lianyi [1 ,3 ]
Hu, Fangzhi [1 ,2 ]
Dong, Jiacheng [2 ]
Zhang, Xiao-Mei [1 ]
Li, Shuai-Shuai [1 ,2 ]
机构：
[1] Chinese Acad Sci, Chengdu Inst Organ Chem, Asymmetr Synth & Chiraltechnol Key Lab Sichuan Pro, Chengdu, Peoples R China
[2] Qingdao Agr Univ, Coll Chem & Pharmaceut Sci, Qingdao 266109, Peoples R China
[3] Univ Chinese Acad Sci, Beijing, Peoples R China
来源：
ORGANIC CHEMISTRY FRONTIERS | 2023年 / 10卷 / 07期
基金：
中国国家自然科学基金;
关键词：
PARA-QUINONE METHIDES; C-H FUNCTIONALIZATION; ASYMMETRIC ALLYLIC DEAROMATIZATION; INTRAMOLECULAR HYDRIDE TRANSFER; C(SP(3))-H BOND; ENANTIOSELECTIVE SYNTHESIS; ALKYLATION; RING; TETRAHYDROQUINOLINES; CONSTRUCTION;
D O I：
10.1039/d3qo00035d
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An aromatization-driven hydride transfer-involved alpha-C(sp(3))-H bond functionalization of the oxygen atom was developed. In this transformation, easily prepared p-quinone methides were applied as aromatic precursors to initiate a [1,5]-hydride transfer/cyclization reaction for generating cyclohexadienone fused spirochromanes. A variety of spirochromanes, including privileged molecules with two spirochromane moieties linked by an alkenyl or a phenyl group, were obtained in high efficiency. In addition, the derivatizations of products were conducted to further enrich the diversity of the structure.
引用
收藏
页码：1796 / 1802
页数：7
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