A general organocatalytic enantioselective malonate addition to alpha,beta-unsaturated enones

Wascholowski V; Knudsen KR; Mitchell CET; Ley SV

首页> 外文期刊>Chemistry: A European journal >A general organocatalytic enantioselective malonate addition to alpha,beta-unsaturated enones

【24h】

A general organocatalytic enantioselective malonate addition to alpha,beta-unsaturated enones

机译：一般的有机催化对映选择性丙二酸酯，除了α，β-不饱和烯酮

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

A general enantioselective organocatalytic conjugate addition procedure of a variety of malonates to alpha,beta-unsaturated enone systems is presented. The reaction is efficiently catalysed by the pyrrolidinyl tetrazole catalyst 1. Cyclic, acyclic and aromatic enones can be used and the reaction with ethyl malonates 3b provides the Michael addition products in high yields with good to excellent enantioselectivities. Since only 1.5 equivalents of malonate are used as a reagent, the reaction is readily scaled and practical to operate. Furthermore, the malonate addition products can be easily mono decarboxylated without loss in enantiomeric excess by enzymatic or sodium hydroxide mediated methods.

机译：提出了各种丙二酸酯向α，β-不饱和烯酮体系的一般对映选择性有机催化共轭加成方法。该反应可通过吡咯烷基四唑催化剂1有效地催化。可以使用环状，无环和芳族烯酮，并且与丙二酸乙酯3b的反应以高收率提供了迈克尔加成产物，具有良好至优异的对映选择性。由于仅使用1.5当量的丙二酸酯作为试剂，因此该反应易于规模化并且操作实用。此外，丙二酸酯加成产物可以通过酶促或氢氧化钠介导的方法容易地单脱羧而不会损失对映体过量。

著录项

来源
《Chemistry: A European journal》 |2008年第20期|共11页
作者
Wascholowski V; Knudsen KR; Mitchell CET; Ley SV;
展开▼
作者单位

展开▼
收录信息
原文格式 PDF
正文语种 eng
中图分类化学;
关键词
asymmetric catalysis; chirality; enantioselectivity; Michael addition; organocatalysis; ASYMMETRIC MICHAEL ADDITION; BETA-KETO-ESTERS; ENZYME CATALYZED-HYDROLYSIS; DIPOLAR APROTIC MEDIA; ALPHA-CYANO ESTERS; PIG-LIVER ESTERASE; CONJUGATE ADDITION; 1; 3-DICARBONYL COMPOUNDS; NITRO-OLEFINS; BIFUNCTIONAL ORGANOCATALYSTS;

机译：不对称催化;手性;对映选择性;迈克尔加成;有机催化;不对称迈克尔加成;BETA-酮酯;酶催化水解;二元非质子传递介质;α-氰基酯;猪肝酯;壳聚糖;壳聚糖;壳聚糖;硝基烯烃;功能性有机催化剂;

相似文献

外文文献
中文文献
专利

1. A general organocatalytic enantioselective malonate addition to alpha,beta-unsaturated enones [J] . Wascholowski V, Knudsen KR, Mitchell CET, Chemistry: A European journal . 2008,第20期

机译：一般的有机催化对映选择性丙二酸酯，除了α，β-不饱和烯酮
2. Organocatalytic Enantioselective Michael Addition of Silyl Malonate to α,β-Unsaturated Enones: One-pot Synthesis of Chiral δ-Keto Esters [J] . Dae Young Kim, Ji Yeon Lee Bulletin of the Korean Chemical Society . 2013,第9期

机译：丙二酸甲硅烷基酯对α，β-不饱和酮的有机催化对映选择性迈克尔加成反应：一锅合成手性δ-酮酯
3. Enantioselective Organocatalytic Michael Addition of Malonates to alpha,beta-Unsaturated Ketones [J] . Li PF, Wen SG, Yu F, Organic letters . 2009,第3期

机译：丙二酸酯的对映选择性有机催化迈克尔加成反应到α，β-不饱和酮上
4. Enantioselective 2+2 Cycloaddition Reaction of 1-Methoxyallenylsilane with alpha-Imino Ester:Chiral Synthesis of alpha,beta-Unsaturated Acylsilanes [C] . Kazunori Daidouji, Kohei Fuchibe, Takahiko Akiyama Symposium on Organometallic Chemistry . 2003

机译：1-甲氧基亚乙烷与α-亚氨基酯的映选择性2 + 2环加入反应：α，β-不饱和酰基硅烷的手性合成
5. Part I. Asymmetric organocatalysis: (1) Direct enantioselective organocatalytic hydroxymethylation of aldehydes catalyzed by alpha,alpha-diphenylprolinol trimethylsilyl ether: Application in the formal synthesis of (-)-Rasfonin; (2) Synthesis of a novel bicyclic secondary amine organocatalyst: Application to the direct enantioselective organocatalytic hydroxymethylation of aldehydes. Part II. Asymmetric synthesis of bicyclic analogues of the anti-osteoporotic drug risedronate. [D] . Miller, John Robert. 2010

机译：第一部分，不对称有机催化：（1）α，α-二苯基脯氨醇三甲基甲硅烷基醚催化的醛的直接对映选择性有机催化羟甲基化：在（-）-Rasfonin的正式合成中的应用；（2）新型双环仲胺有机催化剂的合成：应用于醛的直接对映选择性有机催化羟甲基化。第二部分抗骨质疏松药物Risedronate的双环类似物的不对称合成。
6. Enantioselective Organocatalytic Oxy-Michael Addition to γ/δ-Hydroxy-αβ-enones: Boronate-Amine Complexes as Chiral Hydroxide Synthons [O] . De Run Li, Andiappan Murugan, J. R. Falck -1

机译：γ/δ-羟基-αβ-烯酮的对映选择性有机催化氧-迈克尔加成物：手性氢氧化物合成的硼酸盐-胺配合物
7. 2-Carboxythioester-1,3-dithiane: A Functionalized Masked Carbonyl Nucleophile for the Organocatalytic Enantioselective Michael Addition to Enones [O] . Maurizio Benaglia, Elisabetta Massolo, Davide Brenna, 2016

机译：2-羧基酯-1,3-二脂：官能化蒙型羰基亲核官能团的有机催化映选择性迈克尔

A general organocatalytic enantioselective malonate addition to alpha,beta-unsaturated enones

摘要

著录项

相似文献

相关主题

期刊订阅