Enantioselective Synthesis of Axially Chiral Figure-Eight Spirocycloparaphenylenes via Rh-Catalyzed Intermolecular [2+2+2] Cycloaddition

被引：10
|
作者：
Wang, Li-Hsiang [1 ]
Nogami, Juntaro [1 ]
Nagashima, Yuki [1 ]
Tanaka, Ken [1 ]
机构：
[1] Tokyo Inst Technol, Dept Chem Sci & Engn, Tokyo 1528550, Japan
来源：
ORGANIC LETTERS | 2023年 / 25卷 / 23期
关键词：
CYCLOTRIMERIZATION;
D O I：
10.1021/acs.orglett.3c00895
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We have achieved the enantioselective synthesis of axiallychiralfigure-eight spiro[9.9]-cycloparaphenylene (CPP) tetracarboxylateswith up to 75:25 er via the cationic Rh-(I)/(R)-H-8-BINAP complex-catalyzed chemo-, regio-, and enantioselectiveintermolecular double [2 + 2 + 2] cycloaddition of an achiral symmetrictetrayne with dialkyl acetylenedicarboxylates followed by reductivearomatization. The spiro[9.9]-CPP tetracarboxylates are highly distortedat the phthalate moieties with large dihedral and boat angles andexhibit weak aggregation-induced emission enhancement behavior.
引用
收藏
页码：4225 / 4230
页数：6
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