Palladium catalyzed asymmetric hydrophosphination of alpha,beta- and alpha,beta,gamma,delta-unsaturated malonate esters - efficient control of reactivity, stereo- and regio-selectivity

Yang Xiang-Yuan; Gan Jun Hao; Li Yongxin; Pullarkat Sumod A.; Leung Pak-Hing

首页> 外文期刊>Dalton transactions: An international journal of inorganic chemistry >Palladium catalyzed asymmetric hydrophosphination of alpha,beta- and alpha,beta,gamma,delta-unsaturated malonate esters - efficient control of reactivity, stereo- and regio-selectivity

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Palladium catalyzed asymmetric hydrophosphination of alpha,beta- and alpha,beta,gamma,delta-unsaturated malonate esters - efficient control of reactivity, stereo- and regio-selectivity

机译：钯催化α，β和α，β，γ，δ不饱和丙二酸酯的不对称加氢磷酸化-有效控制反应性，立体和区域选择性

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Both PC-cyclometalated and PCP-pincer type palladium catalysts have recently been found to be robust and efficacious catalysts for the asymmetric P-H addition reaction involving activated olefins. Our studies on the asymmetric P-H addition of diphenylphosphine to malonate ester and alpha,beta,gamma,delta-alkylidenemalonate ester revealed for the first time that the catalyst choice can have a dramatic impact in terms of reactivity as well as regio- and stereo-control for this asymmetric hydrofunctionalization reaction. Besides showing significantly contrasting reactivity and stereoselectivity in the hydrophosphination reaction involving malonate ester, in the case of alpha,beta,gamma,delta-alkylidenemalonate ester, a novel regiodivergent method was developed with the 1,4-adduct being obtained exclusively with the PC-catalyst while the pincer catalyst produced only the 1,6-adduct.

机译：最近发现，对于涉及活化烯烃的不对称P-H加成反应，PC-环金属化和PCP-钳式钯催化剂都是坚固而有效的催化剂。我们对二苯基膦不对称加成丙二酸酯和α，β，γ，δ-亚烷基丙二酸酯的研究首次揭示了催化剂的选择对反应性以及区域和立体控制都有重大影响对于这种不对称的加氢官能化反应。除了在涉及丙二酸酯的加氢磷酸化反应中显示出显着的对比反应性和立体选择性外，在α，β，γ，δ-亚烷基丙二酸酯的情况下，还开发了一种新的区域发散性方法，仅通过PC-获得1，4-加合物催化剂，而钳式催化剂仅产生1,6-加合物。

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《Dalton transactions: An international journal of inorganic chemistry》 |2015年第3期|共6页
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Yang Xiang-Yuan; Gan Jun Hao; Li Yongxin; Pullarkat Sumod A.; Leung Pak-Hing;
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1. Palladium catalyzed asymmetric hydrophosphination of alpha,beta- and alpha,beta,gamma,delta-unsaturated malonate esters - efficient control of reactivity, stereo- and regio-selectivity [J] . Yang Xiang-Yuan, Gan Jun Hao, Li Yongxin, Dalton transactions: An international journal of inorganic chemistry . 2015,第3期

机译：钯催化α，β和α，β，γ，δ不饱和丙二酸酯的不对称加氢磷酸化-有效控制反应性，立体和区域选择性
2. Single-Isomer Tetrasubstituted Olefins from Regioselective and Stereospecific Palladium-Catalyzed Coupling of beta- Chloro-alpha-iodo-alpha,beta-unsaturated Esters [J] . Alison B.Lemay, Katarina S.Vulic, William W.Ogilvie The Journal of Organic Chemistry . 2006,第9期

机译：β-氯-α-碘-α，β-不饱和酯的区域选择性和立体特异性钯催化偶联的单异构体四取代烯烃
3. Single-Isomer Tetrasubstituted Olefins from Regioselective and Stereospecific Palladium-Catalyzed Coupling of beta- Chloro-alpha-iodo-alpha,beta-unsaturated Esters [J] . Alison B.Lemay, Katarina S.Vulic, William W.Ogilvie The Journal of Organic Chemistry . 2006,第9期

机译：β-氯-α-碘-α，β-不饱和酯的区域选择性和立体特异性钯催化偶联的单异构体四取代烯烃
4. Helix Formation in alpha/beta-, alpha/gamma-, and beta/gamma-Hybrid Peptides [C] . Carsten Baldauf, Robert Gunther, Hans-Jorg Hofmann American Peptide Symposium . 2006

机译：α/β-，α-，β/γ-杂交肽中的螺旋形成
5. Asymmetric synthesis of all-carbon alpha-aryl quaternary carbonyl compounds by palladium-catalyzed asymmetric allylic alkylation (Pd-AAA) and their application to the synthesis of biologically important 3,3 '-disubstituted oxindole and alpha-disubstituted quaternary beta-lactone frameworks. [D] . Asad, Md. Sharif A. 2015

机译：钯催化的不对称烯丙基烷基化反应（Pd-AAA）的全碳α-芳基季羰基化合物的不对称合成及其在生物学上重要的3,3'-二取代的羟吲哚和α-二取代的季铵β-内酯骨架的合成中。
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机译：选择性减少。 52.用β-氯二异庚基硼烷或β-甲基苯磺酸有效不对称还原α-炔基α-氟代烷基酮

Palladium catalyzed asymmetric hydrophosphination of alpha,beta- and alpha,beta,gamma,delta-unsaturated malonate esters - efficient control of reactivity, stereo- and regio-selectivity

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