• 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

高催化不对称加成去活化的烷基格氏试剂到醛。

Highly catalytic asymmetric addition of deactivated alkyl grignard reagents to aldehydes.

机构信息

Institute of Biochemistry & Molecular Biology, School of Life Sciences, Lanzhou University, Lanzhou 730000, China.

出版信息

Org Lett. 2009 Dec 17;11(24):5578-81. doi: 10.1021/ol9020942.

DOI:10.1021/ol9020942
PMID:19908888
Abstract

Generally used and highly reactive RMgBr reagents were effectively deactivated by bis[2-(N,N-dimethylamino)ethyl] ether and then were employed in the highly enantioselective addition of Grignard reagents to aldehydes. The reaction was catalyzed by the complex of commercially available (S)-BINOL and Ti(O(i-)Pr)(4) under mild conditions. Compared with the other observed Grignard reagents, alkyl Grignard reagents showed higher enantioselectivity and they achieved >99% ee.

摘要

通常使用且高反应性的 RMgBr 试剂可通过双[2-(N,N-二甲基氨基)乙基]醚有效失活，然后用于格氏试剂对醛的高对映选择性加成。该反应在温和条件下由市售的（S）-BINOL 和 Ti(O(i-)Pr)(4)的配合物催化。与其他观察到的格氏试剂相比，烷基格氏试剂表现出更高的对映选择性，达到了 >99%ee。

相似文献

1
Highly catalytic asymmetric addition of deactivated alkyl grignard reagents to aldehydes.高催化不对称加成去活化的烷基格氏试剂到醛。
Org Lett. 2009 Dec 17;11(24):5578-81. doi: 10.1021/ol9020942.
2
Catalytic highly enantioselective alkylation of aldehydes with deactivated grignard reagents and synthesis of bioactive intermediate secondary arylpropanols.手性催化醛与失活格氏试剂的高对映选择性烷基化反应及生物活性中间体仲芳基丙醇的合成。
J Org Chem. 2010 Oct 15;75(20):6869-78. doi: 10.1021/jo101351t.
3
BINOL-Salen-catalyzed highly enantioselective alkyne additions to aromatic aldehydes.联萘酚-双水杨醛缩乙二胺催化的芳醛的高度对映选择性炔烃加成反应。
Org Lett. 2004 Mar 18;6(6):1065-8. doi: 10.1021/ol0498139.
4
Facile, mild, and highly enantioselective alkynylzinc addition to aromatic aldehydes by BINOL/N-methylimidazole dual catalysis.通过联萘酚/ N -甲基咪唑双催化实现芳醛的简便、温和且高度对映选择性的炔基锌加成反应。
J Org Chem. 2007 Jul 6;72(14):5457-60. doi: 10.1021/jo0707535. Epub 2007 Jun 8.
5
On-step synthesis of a bifunctional BINOL ligand for the highly enantioselective cyanation of aliphatic aldehydes.一步合成用于脂肪醛高度对映选择性氰化反应的双功能联萘酚配体。
Org Lett. 2005 Jun 9;7(12):2381-3. doi: 10.1021/ol050660e.
6
Room temperature and highly enantioselective additions of alkyltitanium reagents to aldehydes catalyzed by a titanium catalyst of (R)-H8-binol.室温下由(R)-H8-联萘酚钛催化剂催化的烷基钛试剂对醛的高度对映选择性加成反应
Chirality. 2011 Nov;23(10):929-39. doi: 10.1002/chir.21018. Epub 2011 Sep 26.
7
3-substituted BINOL Schiff bases and their reductive products for catalytic asymmetric addition of diethylzinc to aldehydes.3-取代的联萘酚席夫碱及其还原产物用于催化二乙基锌对醛的不对称加成反应。
Chirality. 2008 Jul;20(7):828-32. doi: 10.1002/chir.20559.
8
Highly enantioselective vinyl additions of vinylaluminum to ketones catalyzed by a titanium(IV) catalyst of (S)-BINOL.由（S）-联萘酚的钛（IV）催化剂催化的乙烯基铝对酮的高度对映选择性乙烯基加成反应。
Org Lett. 2009 Feb 5;11(3):499-502. doi: 10.1021/ol801999u.
9
Direct asymmetric aldol reaction of aryl ketones with aryl aldehydes catalyzed by chiral BINOL-derived zincate catalyst.手性联萘酚衍生的锌酸盐催化剂催化芳基酮与芳基醛的直接不对称羟醛反应。
J Org Chem. 2008 Sep 19;73(18):7398-401. doi: 10.1021/jo801182n. Epub 2008 Aug 14.
10
Highly enantioselective alkynylation of aldehydes using a new BINOL/Ti(OiPr)4/chiral sulfonamide catalyst system.使用新型联萘酚/四异丙醇钛/手性磺酰胺催化剂体系对醛进行高度对映选择性炔基化反应。
Chirality. 2007 Aug;19(8):638-41. doi: 10.1002/chir.20433.

引用本文的文献

1
Catalytic Enantioselective Addition of Organozirconium Reagents to Aldehydes.手性有机锆试剂对醛的催化对映选择性加成。
Molecules. 2018 Apr 20;23(4):961. doi: 10.3390/molecules23040961.
2
In vivo α-hydroxylation of a 2-alkylindole antagonist of the OXE receptor for the eosinophil chemoattractant 5-oxo-6,8,11,14-eicosatetraenoic acid in monkeys.在猴子体内对嗜酸性粒细胞趋化因子5-氧代-6,8,11,14-二十碳四烯酸的OXE受体的2-烷基吲哚拮抗剂进行α-羟基化。
Biochem Pharmacol. 2017 Aug 15;138:107-118. doi: 10.1016/j.bcp.2017.04.031. Epub 2017 May 3.
3
Grubbs cross-metathesis pathway for a scalable synthesis of γ-keto-α,β-unsaturated esters.
Grubbs 交叉复分解途径用于可扩展合成 γ-酮-α,β-不饱和酯。
J Org Chem. 2014 Feb 7;79(3):1467-72. doi: 10.1021/jo4023606. Epub 2014 Jan 21.