38674-57-6Relevant academic research and scientific papers
Bromomethyl Silicate: A Robust Methylene Transfer Reagent for Radical-Polar Crossover Cyclopropanation of Alkenes
Luo, Wenping,Fang, Yewen,Zhang, Li,Xu, Tianhang,Liu, Yongjun,Li, Yan,Jin, Xiaoping,Bao, Jiakan,Wu, Xiaodong,Zhang, Zongyong
, p. 1778 - 1781 (2020/03/11)
A general protocol for visible-light-induced cyclopropanation of alkenes was developed with bromomethyl silicate as a methylene transfer reagent, offering a robust tool for accessing highly valuable cyclopropanes. In addition to α-aryl or methyl-substituted Michael acceptors and styrene derivatives, the unactivated 1,1-dialkyl ethylenes were also shown to be viable substrates. Apart from realizing the cyclopropanation of terminal alkenes, the methyl transfer reaction has been further demonstrated to be amenable to the internal olefins. The photocatalytic cyclopropanation of 1,3-bis(1-arylethenyl)benzenes was also achieved, giving polycyclopropane derivatives in excellent yields. With late-stage cyclopropanation as the key strategy, the synthetic utility of this transformation was also demonstrated by the total synthesis of LG100268.
Copper(I)-catalyzed carbometalation of nonfunctionalized cyclopropenes using organozinc and grignard reagents
Nakano, Takeo,Endo, Kohei,Ukaji, Yutaka
supporting information, p. 671 - 675 (2015/03/14)
A highly efficient method was developed for the copper(I)-catalyzed carbometalation of various nonfunctionalized and functionalized cyclopropenes. Electrophilic trapping of the cyclopropylmetal intermediates gave multifunctionalized cyclopropanes.
Enantioselective palladium-catalyzed carbozincation of cyclopropenes
Kraemer, Katja,Leong, Paul,Lautens, Mark
, p. 819 - 821 (2011/04/24)
A highly enantioselective palladium-catalyzed carbozincation of cyclopropenes has been developed. The intermediate cyclopropylzinc species, after transmetalation with copper, were trapped with various electrophiles. This one-pot procedure furnished functionalizied cyclopropenes with excellent diastereo-and enantioselectivity.
