Copper-catalyzed asymmetric addition of Et2Zn to 2-cyclohexen-1-one and 2-carbamoyloxy-2-cyclohexen-1-one with phosphoramidite, phosphite, and bidentate phosphite-oxazoline ligands

Chen Yue-Lei; Froehlich Roland; Hoppe Dieter

首页> 外文期刊>Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry >Copper-catalyzed asymmetric addition of Et2Zn to 2-cyclohexen-1-one and 2-carbamoyloxy-2-cyclohexen-1-one with phosphoramidite, phosphite, and bidentate phosphite-oxazoline ligands

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Copper-catalyzed asymmetric addition of Et2Zn to 2-cyclohexen-1-one and 2-carbamoyloxy-2-cyclohexen-1-one with phosphoramidite, phosphite, and bidentate phosphite-oxazoline ligands

机译：铜催化的亚磷酰胺，亚磷酸酯和亚磷酸二齿亚磷酸酯-恶唑啉配体向2-环己烯-1-酮和2-氨基甲酰氧基-2-环己烯-1-酮的铜催化不对称加成反应

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New biphenol-backboned phosphite-oxazoline bidentate ligands were synthesized and applied in the copper-catalyzed asymmetric conjugate additions on 2-cyclohexen-1-one with Et2Zn. In these reactions, the non-chiral oxazoline unit has demonstrated significant impact on the enantioselectivity. 2-Carbamoyloxy-2-cyclohexen-1-one is a new alpha-oxygenated cyclic enone substrate and was synthesized and applied to the aforementioned addition with certain phosphoramidite, phosphite, and the new bidentate ligands. Good ee has been obtained on this substrate.

机译：合成了新的双酚键合亚磷酸酯-恶唑啉双齿配体，并将其用于铜催化的2-环己烯-1-酮与Et2Zn的不对称共轭共轭加成中。在这些反应中，非手性恶唑啉单元已显示出对映选择性的显着影响。 2-氨基甲酰氧基-2-环己烯-1-酮是一种新的α-加氧的环状烯酮底物，被合成并与某些亚磷酰胺，亚磷酸酯和新的二齿配体一起用于上述添加。在该基材上获得了良好的ee。

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《Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry》 |2009年第10期|共6页
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Chen Yue-Lei; Froehlich Roland; Hoppe Dieter;
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1. Copper-catalyzed asymmetric addition of Et2Zn to 2-cyclohexen-1-one and 2-carbamoyloxy-2-cyclohexen-1-one with phosphoramidite, phosphite, and bidentate phosphite-oxazoline ligands [J] . Chen Yue-Lei, Froehlich Roland, Hoppe Dieter Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry . 2009,第10期

机译：铜催化的亚磷酰胺，亚磷酸酯和亚磷酸二齿亚磷酸酯-恶唑啉配体向2-环己烯-1-酮和2-氨基甲酰氧基-2-环己烯-1-酮的铜催化不对称加成反应
2. New bidentate chiral phosphoramidites in copper-catalyzed asymmetric 1,4-addition of diethylzinc to cyclic alpha,beta-enones: enantioselective tandem 1,4-addition-aldol reactions with 2-cyclopentenone [J] . Mandoli A., de Vries AHM., Salvadori P., Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry . 2001,第13期

机译：铜催化二乙基锌向环α，β-烯酮的不对称1,4-加成中的新双齿手性亚磷酰胺：与2-环戊烯酮的对映选择性串联1,4-加成-醛醇反应
3. Highly regioselective asymmetric copper-catalyzed allylic alkylation with dialkylzincs using monodentate chiral spiro phosphoramidite and phosphite ligands [J] . Shi WJ., Wang LX., Fu Y., Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry . 2003,第24期

机译：使用单齿手性螺亚磷酰胺和亚磷酸酯配体与二烷基锌进行高度区域选择性的不对称铜催化的烯丙基烷基化
4. COPPER-CATALYZED ASYMMETRIC CONJUGATE ADDITION WITH CHIRAL SIMPLEPHOS LIGANDS [C] . Laetitia Palais, Alexandre Alexakis European Symposium on Organic Chemistry . 2009

机译：铜催化的不对称缀合物加入手性斯蒂尔菲斯皮特配体
5. I. Highly regioselective diastereoselective directed hydroformylation of allyl ethers. II. Highly practical and enantioselective ligands for copper-catalyzed conjugate addition. [D] . Krauss, Isaac Jonathan. 2003

机译：I.烯丙基醚的高度区域选择性非对映选择性定向加氢甲酰化。二。用于铜催化共轭加成的高度实用和对映选择性配体。
6. An N-Linked Bidentate Phosphoramidite Ligand (N-Me-BIPAM) for Rhodium-Catalyzed Asymmetric 14-Addition of Arylboronic Acids to αβ-Unsaturated Ketones [O] . Yasunori Yamamoto, Kazunori Kurihara, Yoshinori Takahashi, 2013

机译：N链双齿亚磷酰胺配体（N-Me-BIPAM）用于铑催化αβ-不饱和酮上芳基硼酸的不对称14-加成
7. An N-Linked Bidentate Phosphoramidite Ligand (N-Me-BIPAM) for Rhodium-Catalyzed Asymmetric 1,4-Addition of Arylboronic Acids to α,β-Unsaturated Ketones [O] . Yamamoto, Yasunori, Kurihara, Kazunori, Takahashi, Yoshinori, 2013

机译：N链双齿亚磷酰胺配体（N-Me-BIPAM），用于铑催化α，β-不饱和酮上芳基硼酸的不对称1,4-加成

Copper-catalyzed asymmetric addition of Et2Zn to 2-cyclohexen-1-one and 2-carbamoyloxy-2-cyclohexen-1-one with phosphoramidite, phosphite, and bidentate phosphite-oxazoline ligands

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