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Asymmetric Annulation of Donor-Acceptor Cyclopropanes with Dienes
Alternative Title推拉电子环丙烷与共轭二烯的不对称环化反应
Xu H(徐浩)1; Hu JL(胡江林)1; Wang LJ(王丽佳)1; Liao SH(廖赛虎)1; Tang Y(唐勇)1
Source PublicationJ. Am. Chem. Soc.
AbstractAn efficient [4 + 3] cycloaddition reaction of D-A cyclopropanes with dienes has been successfully developed. The reaction proceeds well with various dienolsilyl ethers in the presence of Lewis acid, delivering a variety of cycloheptenes and [n,5,0]carbobicycles with excellent stereoselectivity. The asymmetric version of this reaction is also realized using a newly designed chiral Cy-TOX ligand, providing a new approach to access optically active cycloheptenes and [n,5,0]carbobicycles. Mechanisic study reveals that the reaction involves a stepwise pathway, which undergoes an unusual ring opening of five-membered [3 + 2] intermediate and sequential intramolecular cyclization to afford the thermodynamically stable [4 + 3] annulation product.
Subject Area金属有机化学
Indexed BySCI
WOS IDWOS:000357436300012
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Document Type期刊论文
Corresponding AuthorTang Y(唐勇)
Affiliation1.中科院上海有机化学研究所, 金属有机化学国家重点实验室
Recommended Citation
GB/T 7714
Xu H,Hu JL,Wang LJ,et al. Asymmetric Annulation of Donor-Acceptor Cyclopropanes with Dienes[J]. J. Am. Chem. Soc.,2015,137(25):8006-8009.
APA 徐浩,胡江林,王丽佳,廖赛虎,&唐勇.(2015).Asymmetric Annulation of Donor-Acceptor Cyclopropanes with Dienes.J. Am. Chem. Soc.,137(25),8006-8009.
MLA 徐浩,et al."Asymmetric Annulation of Donor-Acceptor Cyclopropanes with Dienes".J. Am. Chem. Soc. 137.25(2015):8006-8009.
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