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Asymmetric Iridium Catalyzed C-C Coupling of Chiral Diols via Site-Selective Redox-Triggered Carbonyl Addition

机译：通过位点选择性氧化还原引发羰基加成反应的不对称铱催化手性二元醇的C-C偶联

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摘要

Cyclometalated π-allyliridium C,O-benzoate complexes modified by axially chiral chelating phosphine ligands display a pronounced kinetic preference for primary alcohol dehydrogenation, enabling highly site-selective redox-triggered carbonyl additions of chiral primary-secondary 1,3-diols with exceptional levels of catalyst-directed diastereoselectivity. Unlike conventional methods for carbonyl allylation, the present redox-triggered alcohol C-H functionalizations bypass the use of protecting groups, premetalated reagents, and discrete alcohol-to-aldehyde redox reactions.

机译：通过轴向手性螯合膦配体修饰的环金属化π-烯丙基C，O-苯甲酸酯络合物对伯醇脱氢反应具有明显的动力学偏好，从而能够以极高的选择性对手性伯-仲1,3-二醇进行高位点选择性氧化还原触发的羰基添加催化剂导向的非对映选择性。与常规的羰基烯丙基化方法不同，本发明的氧化还原触发的醇C-H官能化绕过了保护基，预金属化试剂和不连续的醇-醛氧化还原反应的使用。

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期刊名称 other
作者
Inji Shin; Michael J. Krische;
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作者单位

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年(卷),期 -1(372),-1
年度 -1
页码 85–101
总页数 20
原文格式 PDF
正文语种
中图分类
关键词
iridium allylation dehydrogenation transfer hydrogenation diastereoselectivity enantioselectivity green chemistry polyketides;

机译：铱;烯丙基化;脱氢;转移氢化;非对映选择性;对映选择性;绿色化学;聚酮;

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专利

1. Iridium-Catalyzed C-C Coupling of a Simple Propargyl Ether with Primary Alcohols: Enantioselective Homoaldol Addition via Redox-Triggered (Z)-Siloxyallylation [J] . Tao Liang, Wandi Zhang, Michael J. Krische Journal of the American Chemical Society . 2015,第51期

机译：简单的炔丙基醚与伯醇的铱催化的C-C偶联：通过氧化还原引发的（Z）-硅氧基烯丙基化的对映选择性高醇醛加成
2. Iridium-catalyzed C-C coupling via transfer hydrogenation: Carbonyl addition from the alcohol or aldehyde oxidation level employing 1,3-cyclohexadiene [J] . Bower JF, Patman RL, Krische MJ Organic letters . 2008,第5期

机译：通过转移氢化进行铱催化的C-C偶联：使用1,3-环己二烯从醇或醛的氧化级加羰基
3. Alkynes as Allylmetal Equivalents in Redox-Triggered C-C Couplings to Primary Alcohols: (Z)-Homoallylic Alcohols via Ruthenium-Catalyzed Propargyl C-H Oxidative Addition [J] . Boyoung Y. Park, Khoa D. Nguyen, Mani Raj Chaulagain, Journal of the American Chemical Society . 2014,第34期

机译：炔烃作为氧化还原引发的C-C偶联至伯醇的烯丙基金属当量：（Z）-通过钌催化的炔丙基C-H氧化加成的均烷醇
4. Iridium Complex-Catalyzed Asymmetric Allylic Alkylation Using Chiral Phosphoramidite Ligands with Oxazolidinone Framework [C] . Gen Onodera, Keijiro Watabe, Yasushi Kawaguchi Symposium on Organometallic Chemistry . 2006

机译：使用具有恶唑烷酮骨架的手性磷酰胺配体的铱络合物催化的不对称烯丙基化烷基化
5. Synthesis and chemistry of iridium complexes containing chiral diphosphine ligands: Oxidative addition to iridium(I) systems and catalytic activity of the electrophilic iridium(III) complexes. [D] . Atesin, Abdurrahman Cagri. 2008

机译：含手性二膦配体的铱配合物的合成与化学：铱（I）系统的氧化加成和亲电铱（III）配合物的催化活性。
6. Iridium Catalyzed C-C Coupling of a Simple Propargyl Ether with Primary Alcohols: Enantioselective Homoaldol Addition via Redox-Triggered (Z)-Siloxyallylation [O] . Tao Liang, Wandi Zhang, Michael J. Krische -1

机译：铱催化的简单丙炔醚与伯醇的C-C偶联：通过氧化还原引发的（Z）-硅氧基烯丙基化的对映选择性高醇醛加成
7. Iridium-Catalyzed C-C Coupling via Transfer Hydrogenation: Carbonyl Addition from the Alcohol or Aldehyde Oxidation Level Employing 1,3-Cyclohexadiene [O] . -1

机译：通过转移氢化铱催化的C-C偶联：羰基从醇或醛氧化水平采用1,3-环己二烯

Asymmetric Iridium Catalyzed C-C Coupling of Chiral Diols via Site-Selective Redox-Triggered Carbonyl Addition

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