Rhodium-catalyzed asymmetric ring opening reactions of oxabicyclic alkenes: Catalyst and substrate studies leading to a mechanistic working model

Lautens M; Fagnou K

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Rhodium-catalyzed asymmetric ring opening reactions of oxabicyclic alkenes: Catalyst and substrate studies leading to a mechanistic working model

机译：铑催化的氧杂双环烯烃的不对称开环反应：催化剂和底物的研究导致了机理的工作模型

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Catalyst and substrate studies have been performed on the rhodium-catalyzed asymmetric ring opening reaction. A working model is advanced that involves oxidative insertion with retention to form an organorhodium intermediate that then undergoes nucleophilic attack with inversion. Kinetic and competition experiments have uncovered evidence for a proton transfer step in the catalytic cycle that may activate both the allylrhodium intermediate and the nucleophile. We have also conducted experiments designed to understand which properties of the PPF-(PBu2)-Bu-t ligand contribute to the high reactivities and enantioselectivities.

机译：已经对铑催化的不对称开环反应进行了催化剂和底物的研究。提出了一种工作模型，该模型涉及具有保留作用的氧化插入，形成有机铑中间体，然后通过倒位进行亲核攻击。动力学和竞争实验发现了催化循环中质子转移步骤的证据，该步骤可能同时激活烯丙基铑中间体和亲核试剂。我们还进行了旨在了解PPF-（PBu2）-Bu-t配体的哪些特性有助于高反应性和对映选择性的实验。

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《Proceedings of the National Academy of Sciences of the United States of America》 |2004年第15期|p.5455-5460|共6页
作者
Lautens M; Fagnou K;
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作者单位

Lautens M, Univ Toronto, Dept Chem, Davenport Res Labs, 80 St George St, Toronto, ON M5S 3H6, Canada;

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收录信息美国《科学引文索引》(SCI);美国《生物学医学文摘》(MEDLINE);美国《化学文摘》(CA);
原文格式 PDF
正文语种 eng
中图分类自然科学总论;
关键词
Chiral ferrocenylamine ligands; Syn-anti dichotomy; Allylic alkylation; Iridium complex; Oxidative addition; (pi-allyl)palladium complexes; Enantiospecific synthesis; Organoboronic acids; Grignard-reagents; Substitution;

机译：手性二茂铁基胺配体;反-二分法;烯丙基烷基化;铱配合物;氧化加成;（π-烯丙基）钯配合物;对映体特异性合成;有机硼酸;格利雅试剂;取代;

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2. Rhodium-Catalyzed Enantioselective Synthesis of Oxazinones via an Asymmetric Ring Opening-Lactonization Cascade of Oxabicyclic Alkenes [J] . Yen Andy, Anh Hoang Pham, Larin Egor M., Organic letters . 2019,第18期

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6. Asymmetric Catalysis Special Feature Part I: Rhodium-catalyzed asymmetric ring opening reactions of oxabicyclic alkenes: Catalyst and substrate studies leading to a mechanistic working model [O] . Mark Lautens, Keith Fagnou 2004

机译：不对称催化的特殊功能（第一部分）：铑催化的氧杂双环烯烃的不对称开环反应：催化剂和底物的研究产生了一种机械的工作模型
7. Rhodium-catalyzed asymmetric ring opening reactions of oxabicyclic alkenes: Catalyst and substrate studies leading to a mechanistic working model [O] . Lautens, Mark, Fagnou, Keith 2004

机译：铑催化的氧杂双环烯烃的不对称开环反应：催化剂和底物的研究导致了机理的工作模型

Rhodium-catalyzed asymmetric ring opening reactions of oxabicyclic alkenes: Catalyst and substrate studies leading to a mechanistic working model

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