QQ客服 官方微博 反馈留言

	SmI(2)-Mediated Radical Cross-Couplings of alpha-Hydroxylated Aza-hemiacetals and N,S-Acetals with alpha,beta-Unsaturated Compounds: Asymmetric Synthesis of (+)-Hyacinthacine A(2), (-)-Uniflorine A, and (+)-7-epi-Casuarine
	Liu, Xue-Kui ; Qiu, Shi ; Xiang, Yong-Gang ; Ruan, Yuan-Ping ; Ruan YP(阮源萍) ; Zheng, Xiao ; Huang, Pei-Qang ; Huang PQ(黄培强)
	2011-05-16
英文摘要	The SmI(2)-mediated radical coupling reactions of beta-hydroxylated pyrrolidine/piperidine aza-hemiacetals 8 and 9 and N,S-acetals 6 and 33 with alpha/beta-unsaturated compounds are described. This method allows a rapid access to beta-hydroxylated pyrrolidines, piperidines, pyrrolizidinones, and indolizidinones. Starting from N,S-acetal 33 and via a common intermediate 27, the alkaloids hyacinthacine A(2) (2), uniflorine A (3, 6-epi-casuarine), and the unnatural epimer 7-epi-casuarine (37) have been synthesized in four and five steps with overall yields of 34%, 16%, and 13%, respectively. The radical mechanism of the coupling reactions has been confirmed by controlled experiments, which also allowed deducing the anionic mechanism in the coupling between N,S-acetal 6 and carbonyl compounds. This demonstrates that the mechanisms of these SmI(2)-mediated reactions are switchable from Barbier-type anionic to radical by cooperative action of BF(3)center dot OEt(2) and t-BuOH.; NSF of China[20402012, 20832005]; National Basic Research Program (973 Program) of China[2010CB833200]; Natural Science Foundation of Fujian Province of China[2010J01050]
语种	英语
出版者	AMER CHEMICAL SOC
内容类型	期刊论文
源URL	[http://dx.doi.org/doi:10.1021/jo200600n]
专题	化学化工－已发表论文
推荐引用方式 GB/T 7714	Liu, Xue-Kui,Qiu, Shi,Xiang, Yong-Gang,et al. SmI(2)-Mediated Radical Cross-Couplings of alpha-Hydroxylated Aza-hemiacetals and N,S-Acetals with alpha,beta-Unsaturated Compounds: Asymmetric Synthesis of (+)-Hyacinthacine A(2), (-)-Uniflorine A, and (+)-7-epi-Casuarine[J],2011.
APA	Liu, Xue-Kui.,Qiu, Shi.,Xiang, Yong-Gang.,Ruan, Yuan-Ping.,阮源萍.,...&黄培强.(2011).SmI(2)-Mediated Radical Cross-Couplings of alpha-Hydroxylated Aza-hemiacetals and N,S-Acetals with alpha,beta-Unsaturated Compounds: Asymmetric Synthesis of (+)-Hyacinthacine A(2), (-)-Uniflorine A, and (+)-7-epi-Casuarine..
MLA	Liu, Xue-Kui,et al."SmI(2)-Mediated Radical Cross-Couplings of alpha-Hydroxylated Aza-hemiacetals and N,S-Acetals with alpha,beta-Unsaturated Compounds: Asymmetric Synthesis of (+)-Hyacinthacine A(2), (-)-Uniflorine A, and (+)-7-epi-Casuarine".(2011).

个性服务

查看访问统计

相关权益政策

暂无数据

收藏/分享

除非特别说明，本系统中所有内容都受版权保护，并保留所有权利。