Hydroxy Group-Enabled Regio- and Stereoselective Hydroalkylation of Alkynyl Cyclobutanol via Palladium-Catalyzed C-C Bond Activation of Cyclopropanol: A One-Step Access to Vinyl Cyclobutanols

被引：0

作者：

Najiar, Lamphiza O. ^{[1
,2
]}

Pati, Bedadyuti Vedvyas ^{[1
,2
]}

Das Adhikari, Gopal Krushna ^{[1
,2
]}

Nanda, Tanmayee ^{[1
,2
]}

Ravikumar, Ponneri C. ^{[1
,2
]}

机构：

[1] Natl Inst Sci Educ & Res NISER, Sch Chem Sci, Bhubaneswar 752050, Odisha, India

[2] Homi Bhabha Natl Inst HBNI, Mumbai 400094, India

来源：

ORGANIC LETTERS | 2024年 / 26卷 / 30期

关键词：

NATURAL-PRODUCTS; CLEAVAGE; CYCLOADDITION; ALKENES;

D O I：

10.1021/acs.orglett.4c01598

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The regio-/stereoselective synthesis of vinyl cyclobutanols from alkynyl cyclobutanols is demonstrated. Here, selective C-C bond activation of the cyclopropyl alcohol ring has been achieved in the presence of the cyclobutanol ring. The KIE experiments indicated the noninvolvement of the O-H oxidative addition step in the rate-determining step. Further, the applicability of these vinyl cyclobutanols for the synthesis of 1,4-diketones and 1,6-diketone is demonstrated.

引用

页码：6314 / 6319

页数：6

共 3 条

[1] Palladium-catalyzed selective C-C bond cleavage and stereoselective alkenylation between cyclopropanol and 1,3-diyne: one-step synthesis of diverse conjugated enynes
Pati, Bedadyuti Vedvyas
Ghosh, Asit
Yadav, Komal
Banjare, Shyam Kumar
Pandey, Shalini
Lourderaj, Upakarasamy
Ravikumar, Ponneri C.
CHEMICAL SCIENCE, 2022, 13 (09) : 2692 - 2700
[2] Rhodium-Catalyzed Room Temperature C-C Activation of Cyclopropanol for One-Step Access to Diverse 1,6-Diketones
Pati, Bedadyuti Vedvyas
Ghosh, Asit
Ravikumar, P. C.
ORGANIC LETTERS, 2020, 22 (07) : 2854 - 2860
[3] Direct Assembly of Diverse Unsymmetrical Tertiary 9-Fluorenols via Transient Directing Group-Enabled Palladium-Catalyzed Dual C-H Bond Activation of α-Ketoesters
Xu, Wengang
Zhang, Yangyang
Wu, Yongdi
Wang, Jian
Wu, Xuelian
Zhou, Yirong
Zhang, Fang-Lin
JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (16): : 10807 - 10814

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