Highly Enantioselective Organocatalytic Addition of Aldehydes to N-(Phenylmethylene)benzamides: Asymmetric Synthesis of the Paclitaxel Side Chain and Its Analogues

Dziedzic P; Schyman P; Kullberg M; Cordova A

首页> 外文期刊>Chemistry: A European journal >Highly Enantioselective Organocatalytic Addition of Aldehydes to N-(Phenylmethylene)benzamides: Asymmetric Synthesis of the Paclitaxel Side Chain and Its Analogues

【24h】

Highly Enantioselective Organocatalytic Addition of Aldehydes to N-(Phenylmethylene)benzamides: Asymmetric Synthesis of the Paclitaxel Side Chain and Its Analogues

机译：醛对N-（苯基亚甲基）苯甲酰胺的高度对映选择性有机催化加成反应：紫杉醇侧链的不对称合成及其类似物

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 simple highly enantioselective organocatalytic addition of aldehydes to N-(phenylmethylene)benzamides is presented. The application of (R)-proline as the catalyst and subsequent oxidation of the protected alpha-hydroxy-beta-benzoylaminoaldehydes (92%-99% ee) gives access to esterification-ready phenylisoserine derivatives such as the protected paclitaxel (taxol) side chain. Esterification of these derivatives with baccatin III gives access to the cancer chemotherapeutic substance paclitaxel and its analogues that do not exist in nature.

机译：提出了向N-（苯基亚甲基）苯甲酰胺的醛的简单高对映选择性有机催化加成。（R）脯氨酸作为催化剂的应用以及随后对受保护的α-羟基-β-苯甲酰氨基醛（92％-99％ee）的氧化可得到易于酯化的苯基异丝氨酸衍生物，例如受保护的紫杉醇（紫杉醇）侧链。用浆果赤霉素III酯化这些衍生物使人们获得了自然界中不存在的癌症化疗物质紫杉醇及其类似物。

著录项

来源
《Chemistry: A European journal》 |2009年第16期|共5页
作者
Dziedzic P; Schyman P; Kullberg M; Cordova A;
展开▼
作者单位

展开▼
收录信息
原文格式 PDF
正文语种 eng
中图分类应用化学;
关键词
aldehydes; asymmetric catalysis; (phenylmethylene)benzamides; organocatalysis; taxol;

机译：醛;不对称催化;（苯基亚甲基）苯甲酰胺;有机催化;紫杉醇;

相似文献

外文文献
中文文献
专利

1. Highly Enantioselective Organocatalytic Addition of Aldehydes to N-(Phenylmethylene)benzamides: Asymmetric Synthesis of the Paclitaxel Side Chain and Its Analogues [J] . Dziedzic P, Schyman P, Kullberg M, Chemistry: A European journal . 2009,第16期

机译：醛对N-（苯基亚甲基）苯甲酰胺的高度对映选择性有机催化加成反应：紫杉醇侧链的不对称合成及其类似物
2. Highly enantioselective organocatalytic addition of unmodified aldehydes to N-Boc protected imines:one-pot asymmetric synthesis of beta-amino acids [J] . Jan Vesely, Ramon Rios, Ismail Ibrahem Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2007,第26期

机译：未修饰醛对N-Boc保护的亚胺的高度对映选择性有机催化加成：一锅不对称合成β-氨基酸
3. Synthesis of 3-substituted 1,5-aldehyde esters via an organocatalytic highly enantioselective conjugate addition of new carbonylmethyl 2-pyridinylsulfone to enals [J] . Jing Deng, Fei Wang, Wenzhong Yan, Chemical Communications . 2012,第1期

机译：通过新的羰基甲基2-吡啶基砜的有机催化高对映选择性共轭加成反应，合成3-取代的1,5-醛酯
4. Enantioselective Organocatalytic Michael Addition of Aldehydes to β-Nitrostyrenes [C] . Marju Laars, Kerti Ausmees, Tonis Kanger European Symposium on Organic Chemistry . 2009

机译：对β-硝化丁烯的映选择性有机催化迈克尔添加醛
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. Organocatalytic Enantioselective Conjugate Addition of Nitromethane to Benzylidene-2-Benzoyl Acetate: Asymmetric Synthesis of ABT – 627 an Endothelin Receptor Antagonist [O] . Saumen Hajra, Sk Mohammad Aziz, Bibekananda Jana, 2020

机译：硝基甲烷对苄基-2-苄基乙酸酯的有机催化对映选择性共轭加成：内皮素受体拮抗剂ABT – 627的不对称合成。
7. Enantioselective synthesis of gabapentin analogues via organocatalytic asymmetric Michael addition of α-branched aldehydes to β-nitroacrylates [O] . Yoshida, Masanori, Masaki, Erika, Ikehara, Hiroto, 2012

机译：通过将α-支化醛基有机催化不对称迈克尔加成到β-硝基丙烯酸酯中来加巴喷丁类似物的对映选择性合成

Highly Enantioselective Organocatalytic Addition of Aldehydes to N-(Phenylmethylene)benzamides: Asymmetric Synthesis of the Paclitaxel Side Chain and Its Analogues

摘要

著录项

相似文献

相关主题

期刊订阅