The Use of Polymer-Bound Triphenylphosphine in the Stereochemical Inversion of Secondary Alcohols

J. M. White A. R. Tunoori D. Dutta G. I. Georg

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The Use of Polymer-Bound Triphenylphosphine in the Stereochemical Inversion of Secondary Alcohols

机译：聚合物结合的三苯膦在仲醇的立体化学转化中的应用

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Polymer-bound triphenylphosphine can replace triphenylphosphine in the Mitsunobu reaction to generate stereochemically inverted secondary alcohols. This method is comparable with the standard Mitsunobu reaction in terms of inversion of stereochemistry, yield, and reaction time, even for sterically very hindered secondary alcohols. The special merit of this reaction is that the excess polymer-bound triphenylphosphine and its by-products are easily removed by filtration from the reaction products.

机译：与聚合物结合的三苯膦可以在Mitsunobu反应中取代三苯膦，生成立体化学上反转的仲醇。就立体化学的转化，产率和反应时间而言，即使对于空间非常受阻的仲醇，该方法也可与标准的Mitsunobu反应相媲美。该反应的特殊优点是过量的与聚合物结合的三苯膦及其副产物易于通过过滤从反应产物中除去。

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来源
《Combinatorial Chemistry & High Throughput Screening》 |2000年第2期|p.103-106|共4页
作者
J. M. White A. R. Tunoori D. Dutta G. I. Georg;
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作者单位

Department of Medicinal Chemistry and The Drug Discovery Program, Higuchi Biosciences Center, University of Kansas, Lawrence, KS 66045, USA;

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正文语种 eng
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关键词
Polymer bound triphenylphosphine, Mitsunobu reaction, Diethyl azodicarboxylate, Lithium hydroxide, Tetrahydrofuran;

机译：聚合物键合的三苯膦;Mitsunobu反应;偶氮二羧酸二乙酯;氢氧化锂;四氢呋喃;

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专利

1. Deracemization of 1,2-diol monotosylate derivatives by a combination of enzymatic hydrolysis with the Mitsunobu inversion using polymer-bound triphenylphosphine [J] . Yasutaka Shimada, Kazumasa Usuda, Hirokazu Okabe, Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry . 2010,第24期

机译：通过与聚合物结合的三苯基膦进行酶促水解和Mitsunobu转化的组合，对1,2-二醇单甲苯磺酸酯衍生物进行脱氨
2. Triruthenium dodecacarbonyl/triphenylphosphine catalyzed dehydrogenation of primary and secondary alcohols [J] . Meijer RH., Ligthart GBWL., Meuldijk J., Tetrahedron . 2004,第5期

机译：十二碳三钌/三苯基膦催化的伯醇和仲醇脱氢
3. Stereochemical preference of Candida parapsilosis ATCC 7330 mediated deracemization: E- versus Z-aryl secondary alcohols [J] . Saravanan T., Selvakumar R., Doble M., Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry . 2012,第18a19期

机译：副念珠菌ATCC 7330介导的去消旋作用的立体化学偏好：E-与Z-芳基仲醇
4. Stereochemical Control of Asymmetric Reduction by Deleting an Alcohol Gehydrogenase Gene of a Cyanobacterium [C] . Hisataka Ohta, Kenjro Suzuki, Tetsuo Takemura, Photosynthesis research for food, fuel and future . 2010

机译：立体化学控制的不对称还原，通过删除蓝藻的酒精脱氢酶基因。
5. Part I. One-pot synthesis of secondary alcohols and one-pot asymmetric synthesis of secondary propargylic alcohols. Part II. Redox isomerization of secondary propargylic alcohols to enones. Part III. Synthesis study towards C9-C14 fragment of (+)-discodermolide. Part IV. Asymmetric synthesis of anti, anti-stereotriad building blocks for polypropionate natural products [D] . Xie, Qiuzhe 2007

机译：第一部分：仲醇的一锅法合成和仲炔丙醇的一锅法不对称合成。第二部分仲炔丙醇的氧化还原异构化为烯酮。第三部分（+）-discodermolide C9-C14片段的合成研究。第四部分聚丙烯酸酯天然产物的抗，抗立体三环构建基的不对称合成
6. Structural insights into stereochemical inversion by diaminopimelate epimerase: An antibacterial drug target [O] . Bindu Pillai, Maia M. Cherney, Christopher M. Diaper, 2006

机译：二氨基庚二酸酯差向异构酶对立体化学转化的结构见解：抗菌药物的靶标
7. Triruthenium dodecacarbonyl/triphenylphosphine catalyzed dehydrogenation of primary and secondary alcohols [O] . Meijer, RH Renzo, Ligthart, GBWL Ronald, Meuldijk, J Jan, 2004

机译：十二碳三钌/三苯基膦催化的伯醇和仲醇脱氢
8. Photoactivation of Cluster Catalysis: A Comparison of 1-Pentene Isomerization by Tetracarbonyl(Triphenylphosphine)Ruthenium and 1,1,1,2,2,2,3,3,3- Nonacarbonyl-1,2,3-Tris(Triphenylphosphine)-Triangulo-Triruthenium. [R] . Graff, J. L., Sanner, R. D., Wrighton, M. S. 1978

机译：簇催化的光活化：四羰基（三苯基膦）钌和1,1,1,2,2,2,3,3-非羰基-1,2,3-三（三苯基膦）的1-戊烯异构化比较 - Triangulo-三钌。

The Use of Polymer-Bound Triphenylphosphine in the Stereochemical Inversion of Secondary Alcohols

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