• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利：CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法，用中文像聊天一样搜索，搜遍4000万医学文献。AI智能推荐，让科研检索更轻松。

立即免费搜索

文件翻译

保留排版，准确专业，支持PDF/Word/PPT等文件格式，支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述，25分钟生成高质量综述，智能提取关键信息，辅助科研写作。

立即免费体验

Asymmetric [2,3]-Wittig rearrangement induced by a chiral carbanion whose chirality was transferred from an epoxide.

作者信息

Sasaki Michiko, Higashi Mariko, Masu Hyuma, Yamaguchi Kentaro, Takeda Kei

机构信息

Department of Synthetic Organic Chemistry, Graduate School of Medical Sciences, Hiroshima University, 1-2-3 Kasumi, Minami-Ku, Hiroshima 734-8551, Japan.

出版信息

Org Lett. 2005 Dec 22;7(26):5913-5. doi: 10.1021/ol052544h.

DOI:10.1021/ol052544h
PMID:16354098
Abstract

[reaction: see text] The enantioselective [2,3]-Wittig rearrangement of 1-allyloxy-1-(naphthalen-2-yl)-4-siloxy-2,4-pentadienyl anion, derived from optically enriched 4,5-epoxy-1-(naphthalen-2-yl)-5-silyl-2-pentenyl allyl ether via a base-induced ring opening of the epoxide followed by Brook rearrangement, has been studied. The chirality of the epoxide was transferred to the alcohols in up to 97% ee, depending on the solvent used. The best result was obtained in 1,4-dioxane at a temperature above room temperature.

摘要

相似文献

1
Asymmetric [2,3]-Wittig rearrangement induced by a chiral carbanion whose chirality was transferred from an epoxide.
Org Lett. 2005 Dec 22;7(26):5913-5. doi: 10.1021/ol052544h.
2
Nitrile anion cyclization with epoxysilanes followed by Brook rearrangement/ring-opening of cyclopropane nitriles/alkylation.腈基阴离子与环氧硅烷环化，随后进行布鲁克重排/环丙烷腈的开环/烷基化反应。
J Org Chem. 2005 Dec 9;70(25):10515-23. doi: 10.1021/jo0519413.
3
Nitrile anion cyclization with epoxysilanes followed by brook rearrangement/ring opening of cyclopropane nitriles/alkylation.腈基阴离子与环氧硅烷环化，随后进行布鲁克重排/环丙烷腈的开环/烷基化反应。
Org Lett. 2004 Aug 19;6(17):2973-5. doi: 10.1021/ol048817a.
4
Tandem base-promoted ring-opening/Brook rearrangement/allylic alkylation of O-silyl cyanohydrins of beta-silyl-alpha,beta-epoxyaldehyde: scope and mechanism.β-硅基-α,β-环氧醛的O-硅基氰醇的串联碱促进开环/布鲁克重排/烯丙基烷基化：范围和机理
J Org Chem. 2003 Nov 28;68(24):9330-9. doi: 10.1021/jo0352934.
5
Epoxysilane rearrangement induced by a carbanion generated by conjugate addition of enolates of chloroacetate and alpha-chloroacetamides: formation of functionalized cyclopropane derivatives.氯乙酸酯和α-氯代乙酰胺烯醇化物共轭加成产生的碳负离子引发的环氧硅烷重排：官能化环丙烷衍生物的形成
Org Lett. 2006 Apr 27;8(9):1889-91. doi: 10.1021/ol060469k.
6
Formation of functionalized carbocycles via base-promoted ring opening/Brook rearrangement/allylic alkylation of gamma-silyl-beta,gamma-epoxybutanenitrile followed by nitrile anion cyclization with bis-electrophiles.通过碱促进的γ-硅基-β,γ-环氧丁腈的开环/布鲁克重排/烯丙基烷基化，随后腈阴离子与双亲电试剂进行环化反应，形成官能化碳环。
Org Lett. 2004 Nov 11;6(23):4367-9. doi: 10.1021/ol048100n.
7
Stereocontrolled construction of seven-membered carbocycles using a combination of Brook rearrangement-mediated [3 + 4] annulation and epoxysilane rearrangement.
J Org Chem. 2007 Feb 16;72(4):1379-87. doi: 10.1021/jo062282c. Epub 2007 Jan 23.
8
Asymmetric double ring-opening of a C(2h)-symmetric bis-epoxide: improved enantiomeric excess of the product through enantioselective desymmetrisation and 'proof-reading' steps.C(2h)对称双环氧化合物的不对称双开环反应：通过对映选择性去对称化和“校对”步骤提高产物的对映体过量。
Org Biomol Chem. 2005 Jun 21;3(12):2350-3. doi: 10.1039/b504972e. Epub 2005 May 23.
9
[Development and synthetic application of epoxysilane rearrangement].[环氧硅烷重排的发展与合成应用]
Yakugaku Zasshi. 2008 Aug;128(8):1169-77. doi: 10.1248/yakushi.128.1169.
10
External chiral ligand-induced enantioselective versions of the [2,3]-Wittig sigmatropic rearrangement.外消旋手性配体诱导的[2,3]-维蒂希σ迁移重排的对映选择性变体。
Chirality. 2000 Jun;12(5-6):505-9. doi: 10.1002/(SICI)1520-636X(2000)12:5/6<505::AID-CHIR36>3.0.CO;2-3.

引用本文的文献

1
Application of Biobased Solvents in Asymmetric Catalysis.生物基溶剂在不对称催化中的应用。
Molecules. 2022 Oct 8;27(19):6701. doi: 10.3390/molecules27196701.