中国科学院上海有机化学研究所机构知识库
Advanced  
SIOC OpenIR  > 中科院有机氟化学重点实验室  > 期刊论文
学科主题: 氟化学
题名: An efficient and general route to gem-difluoromethylenated alpha,beta-unsaturated delta-lactones: High enantioselective synthesis of gem-difluoromethylenated goniothalamins
其他题名: 一种高效和通用的合成二氟亚甲基a,b-不饱和内酯的方法:高对映选择性的合成二氟亚甲基的Goniothalamins
作者: You ZW(游正伟) ; Jiang ZX(江中兴) ; Wang BL(王柄林) ; Qing FL(卿凤翎)
通讯作者: 卿凤翎
刊名: J. Org. Chem.
发表日期: 2006
卷: 71, 期:19, 页:7261-7267
收录类别: SCI
部门归属: 中科院上海有机化学研究所; 东华大学
英文摘要: An efficient and general strategy to gem-difluoromethylenated alpha,beta-unsaturated delta-lactones in high yields from various aldehydes (including aliphatic, aromatic, alpha,beta-unsaturated, and sterically hindered aldehydes) has been developed. This methodology was successfully applied for the preparation of two enantiomers of gem-difluoromethylenated goniothalamins (S)-1 and (R)-1. gem-Difluoropropargylation of cinnamaldehyde followed by the resolution of resulting homopropargylic alcohols mediated by lipase from Pseudomonas (AK) gave alcohols (R)-6 and (S)-6. Selective hydrogenation of the triple bond of (S)-6 and (R)-6 to double bond with Lindlar catalyst in the presence of quinoline afforded the expected product (S)-8 and (R)-8, respectively. Deprotection of (S)-8 and (R)-8 followed by oxidation of the resulting 1,5-diols with catalytic 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO) and excess bis-acetoxyiodobenzene (BAIB) provided the target molecules gem-difluoromethylenated goniothalamins (S)-1 and (R)-1 in high yields, respectively.
语种: 英语
相关网址: 查看原文
WOS记录号: WOS:000240371900015
Citation statistics:
内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/17567
Appears in Collections:中科院有机氟化学重点实验室_期刊论文

Files in This Item: Download All
File Name/ File Size Content Type Version Access License
2006049.pdf(158KB)----开放获取--View Download

Recommended Citation:
You ZW,Jiang ZX,Wang BL,et al. An efficient and general route to gem-difluoromethylenated alpha,beta-unsaturated delta-lactones: High enantioselective synthesis of gem-difluoromethylenated goniothalamins[J]. J. Org. Chem.,2006,71(19):7261-7267.
Service
Recommend this item
Sava as my favorate item
Show this item's statistics
Export Endnote File
Google Scholar
Similar articles in Google Scholar
[游正伟]'s Articles
[江中兴]'s Articles
[王柄林]'s Articles
CSDL cross search
Similar articles in CSDL Cross Search
[游正伟]‘s Articles
[江中兴]‘s Articles
[王柄林]‘s Articles
Related Copyright Policies
Null
Social Bookmarking
Add to CiteULike Add to Connotea Add to Del.icio.us Add to Digg Add to Reddit
文件名: 2006049.pdf
格式: Adobe PDF
此文件暂不支持浏览
所有评论 (0)
暂无评论
 
评注功能仅针对注册用户开放,请您登录
您对该条目有什么异议,请填写以下表单,管理员会尽快联系您。
内 容:
Email:  *
单位:
验证码:   刷新
您在IR的使用过程中有什么好的想法或者建议可以反馈给我们。
标 题:
 *
内 容:
Email:  *
验证码:   刷新

Items in IR are protected by copyright, with all rights reserved, unless otherwise indicated.

 

 

Valid XHTML 1.0!
Powered by CSpace