Heteroatom-Guided Torquoselective Olefination of alpha-Oxy and alpha-Amino Ketones via Ynolates

Mitsuru Shindo; Takashi Yoshikawa; Kozo Shishido; Yasuaki Itou; Seiji Mori; Takeshi Nishii

首页> 外文期刊>Chemistry: A European journal >Heteroatom-Guided Torquoselective Olefination of alpha-Oxy and alpha-Amino Ketones via Ynolates

【24h】

Heteroatom-Guided Torquoselective Olefination of alpha-Oxy and alpha-Amino Ketones via Ynolates

机译：异戊二醛引导的羟甲酸酯类对α-氧和α-氨基酮的甲苯磺酰化选择性烯烃化

获取原文

获取原文并翻译 | 示例

掌桥外文数据库（机构版） >>

开具论文收录证明 >>

文献代查 >>

页面导航

摘要
著录项
相似文献
相关主题

摘要

Ynolates were found to react with alpha-alkoxy-,alpha-siloxy-,and alpha-arylox-yketones at room temperature to afford tetrasubstituted olefins with high Z selectivity.Since the geometrical selectivity was determined in the ring opening of the beta-lactone enolate intermediates,the torquoselectivity was controlled by the ethereal oxygen atoms.From experimental and theoretical studies,the high Z selectivity is induced by orbital and steric interactions rather than by chelation.In a similar manner,alpha-dialkylamino ketones provided olefins with excellent Z selectivity.These products can be easily converted into multisubstituted buteno-lides and gamma-butyrolactams in good yield.

机译：发现壬酸酯在室温下会与α-烷氧基-，α-甲硅烷氧基-和α-芳氧基-酮反应，从而得到具有高Z选择性的四取代烯烃。由于在β-内酯烯酸酯的开环中确定了几何选择性通过实验和理论研究，高Z选择性是通过轨道和空间相互作用而不是通过螯合诱导的。以类似的方式，α-二烷基氨基酮为烯烃提供了极佳的Z选择性。这些产物可以容易地以良好的产率转化为多取代的丁烯内酯和γ-丁内酰胺。

著录项

来源
《Chemistry: A European journal》 |2006年第2期|共13页
作者
Mitsuru Shindo; Takashi Yoshikawa; Kozo Shishido; Yasuaki Itou; Seiji Mori; Takeshi Nishii;
展开▼
作者单位

展开▼
收录信息
原文格式 PDF
正文语种 eng
中图分类
关键词
density functional calculations; ketones; olefination; torquoselectivity; ynolates;

机译：密度泛函计算酮烯化扭转选择性合成物;

相似文献

外文文献
中文文献
专利

1. Heteroatom-Guided Torquoselective Olefination of alpha-Oxy and alpha-Amino Ketones via Ynolates [J] . Mitsuru Shindo, Takashi Yoshikawa, Kozo Shishido, Chemistry: A European journal . 2006,第2期

机译：异戊二醛引导的羟甲酸酯类对α-氧和α-氨基酮的甲苯磺酰化选择性烯烃化
2. The Effect Of Alkynyl Groups On Torquoselectivity. Highly Stereoselective Olefination Of Alkynyl Ketones With Ynolates [J] . Takashi Yoshikawa, Seiji Mori, Mitsuru Shindo Journal of the American Chemical Society . 2009,第6期

机译：炔基对Torquoselectivity的影响。炔丙酸酯对炔酮的高度立体选择性烯烃化
3. The effects of C-S and C-Se bonds on torquoselectivity: stereoselective olefination of alpha-thio and alpha-selenoketones with ynolates [J] . Yoshikawa T, Mori S, Shindo M Tetrahedron . 2009,第43期

机译：C-S和C-Se键对torquoselectivity的影响：α-硫代和α-硒代酮与炔诺酸酯的立体选择性烯化
4. Part I: Asymmetric synthesis of alpha-allyl-alpha-aryl alpha-amino acids. Part II: Asymmetric spirocyclization of allenyl ketones. Part III: Chemoselective activation of C(sp3)--H bond over C(sp 2)--H bond with Pd(II). [D] . Curto, John M. 2014

机译：第一部分：α-烯丙基-α-芳基α-氨基酸的不对称合成。第二部分：烯基酮的不对称螺环化。第三部分：与Pd（II）相比，C（sp3）-H键的化学选择性活化。
5. A Torquoselective Extrusion of Isoxazoline N-Oxides. Application to the Synthesis of Aryl Vinyl and Divinyl Ketones for Nazarov Cyclization [O] . Daniel P. Canterbury, Ildiko R. Herrick, Joann Um, -1

机译：异恶唑啉N-氧化物的甲Torquoselective挤出。应用芳基乙烯和二乙烯基酮的环化纳扎罗夫的合成
6. Toyquoselective Olefination with Ynolates [O] . Mitsuru Shindo, Seiji Mori 2008

机译：用菱盐的ToyquosElective olyination

Heteroatom-Guided Torquoselective Olefination of alpha-Oxy and alpha-Amino Ketones via Ynolates

摘要

著录项

相似文献

相关主题

期刊订阅