Catalytic enantioselective synthesis of benzocyclobutenols and cyclobutanols via a sequential reduction/C-H functionalization

被引：13
|
作者：
Chen, Jun [1 ]
Shi, Zhan [1 ]
Li, Chunyu [1 ,2 ]
Lu, Ping [1 ]
机构：
[1] Fudan Univ, Res Ctr Mol Recognit & Synth, Dept Chem, 220 Handan Lu, Shanghai 200433, Peoples R China
[2] Scripps Res Inst, Dept Chem, 10550 North Torrey Pines Rd, La Jolla, CA 92037 USA
来源：
CHEMICAL SCIENCE | 2021年 / 12卷 / 31期
基金：
中国国家自然科学基金;
关键词：
ASYMMETRIC TRANSFER HYDROGENATION; STEREOSELECTIVE-SYNTHESIS; DERIVATIVES; ACTIVATION; DESYMMETRIZATION; CONSTRUCTION;
D O I：
10.1039/d1sc02119b
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
We report here a sequential enantioselective reduction/C-H functionalization to install contiguous stereogenic carbon centers of benzocyclobutenols and cyclobutanols. This strategy features a practical enantioselective reduction of a ketone and a diastereospecific iridium-catalyzed C-H silylation. Further transformations have been explored, including controllable regioselective ring-opening reactions. In addition, this strategy has been utilized for the synthesis of three natural products, phyllostoxin (proposed structure), grandisol and fragranol.
引用
收藏
页码：10598 / 10604
页数：7
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