Facile synthesis of optically active oxindoles by copper-catalyzed asymmetric monotosylation of prochiral 1,3-diols

Kuriyama M.; Tanigawa S.; Kubo Y.; Demizu Y.; Onomura O.

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Facile synthesis of optically active oxindoles by copper-catalyzed asymmetric monotosylation of prochiral 1,3-diols

机译：铜催化前手性1,3-二醇的不对称单糖基化反应可轻松合成旋光性羟吲哚

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摘要

A facile synthetic method toward optically active 3,3-disubstituted oxindoles with excellent enantioselectivity was achieved using chiral copper-catalyzed desymmetrization of prochiral 1,3-diols. The monotosylated product was transformed into oxindole derivatives efficiently.

机译：利用前手性1,3-二醇的手性铜催化脱对称，实现了一种简便的合成方法，该方法可制备具有良好对映选择性的旋光3,3-二取代的羟吲哚。单甲苯基化产物被有效地转化为羟吲哚衍生物。

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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》 |2010年第12期|共4页
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Kuriyama M.; Tanigawa S.; Kubo Y.; Demizu Y.; Onomura O.;
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1. Facile synthesis of optically active oxindoles by copper-catalyzed asymmetric monotosylation of prochiral 1,3-diols [J] . Kuriyama M., Tanigawa S., Kubo Y., Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry . 2010,第11a12期

机译：铜催化前手性1,3-二醇的不对称单糖基化反应可轻松合成旋光性羟吲哚
2. Synthesis of optically active oxazoline derivatives via catalytic asymmetric desymmetrization of 1,3-diols [J] . Tsuda Y., Kuriyama M., Onomura O. Chemistry: A European journal . 2012,第9期

机译：1,3-二醇催化不对称脱对称合成旋光恶唑啉衍生物
3. Chiral synthesis via organoboranes. 45. Asymmetric hydroboration of 1-cyclopentenol derivatives using diisopinocampheylborane. Synthesis of optically active cyclopentane-1,2-diol derivatives of high optical purity [J] . Herbert C. Brown, Dhanabalan Murali, Bakthan Singaram Journal of Organometallic Chemistry . 1999,第1a2期

机译：通过有机硼烷进行手性合成。 45.使用二异op基樟脑硼烷对1-环戊烯醇衍生物进行不对称硼氢化。高光学纯度的光学活性环戊烷-1,2-二醇衍生物的合成
4. Synthesis of Pseudo Glycopeptides Using 1,3-Diol Derivative [C] . Ito Y., Tomabechi Y., Inazu T. International Carbohydrate Symposium . 2013

机译：使用1,3-二醇衍生物合成假糖肽
5. Asymmetric synthesis of 1,3-anti-diol containing subunits using phosphorus-based tethers: Application in the total synthesis of dolabelide C [D] . Thomas, Christopher Daniel 2010

机译：基于磷系链的不对称合成含1,3-抗二醇的亚基：在多标签肽C的全合成中的应用
6. Facile Synthesis of Optically Active Imidazole Derivatives [O] . Ales Marek, Jiri Kulhanek, Miroslav Ludwig, 2007

机译：光学活性咪唑衍生物的简便合成
7. Facile synthesis of optically active oxindoles by copper-catalyzed asymmetric monotosylation of prochiral 1,3-diols [O] . Kuriyama Masami, Tanigawa Satoko, Kubo Yuki, 2010

机译：通过铜催化的前手性1,3-二醇的不对称单亚胺化来简便地合成光学活性的羟吲哚
8. Chiral Synthesis via Organoboranes. 15. Selective Reductions. 42. Asymmetric Reduction of Representative Prochiral Ketones with Potassium 9-O-(1,2:5,6-Di-O-isopropylidene-alpha-D-glucofuranosyl)-9- boratabicyclo(3.3.1)-nonane [R] . Brown, H. C., Cho, B. T., Park, W. S. 1988

机译：有机硼烷的手性合成。 15.选择性减少。 42.用9-O-（1,2：5,6-二-O-异亚丙基-α-D-葡呋喃糖基）-9-硼三环（3.3.1） - 壬烷钾不对称还原代表性前手性酮

Facile synthesis of optically active oxindoles by copper-catalyzed asymmetric monotosylation of prochiral 1,3-diols

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