Competition of (3+2) annulation and (3+2) cycloaddition in the reaction of alkenes with donor-acceptor cyclopropanes

被引：0

作者：

Volkova, Yu. A. ^{[1
]}

Boichenko, M. A. ^{[2
]}

Shorokhov, V. V. ^{[2
]}

Zhokhov, S. S. ^{[2
]}

Andreev, I. A. ^{[3
]}

Ratmanova, N. K. ^{[3
]}

Trushkov, I. V. ^{[1
]}

Ivanova, O. A. ^{[2
]}

机构：

[1] Russian Acad Sci, ND Zelinsky Inst Organ Chem, 47 Leninsky Prosp, Moscow 119991, Russia

[2] Lomonosov Moscow State Univ, Dept Chem, Build 3,1 Leninskie Gory, Moscow 119991, Russia

[3] Dmitry Rogachev Natl Med Res Ctr Pediat Hematol On, 1 Ul Samory Mashela, Moscow 117997, Russia

来源：

RUSSIAN CHEMICAL BULLETIN | 2024年 / 73卷 / 05期

关键词：

donor-acceptor cyclopropanes; Lewis acids; (3+2) cycloaddition; (3+2) annulation; cyclopentanes; indanes; ENOL SILYL ETHERS; CONSTRUCTION; TUBULIN;

D O I：

10.1007/s11172-024-4240-8

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Lewis acid-initiated reaction of (het)aryl-substituted donor-acceptor cyclopropanes with styrenes was studied. The initiation of the process by tin(IV) chloride caused the reaction to proceed in two alternative directions, namely, with the formation of substituted cyclopentanes ((3+2) cycloaddition products) and substituted indanes or their hetero analogs ((3+2) annulation products). The chemoselectivity of the reaction was controlled by several factors, such as the reaction conditions and the nature of reacting compounds and initiator.

引用

页码：1237 / 1252

页数：16

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