New Silicon Groups as Potential Chiral Auxiliaries. Synthesis and Highly Selective Chiral 1,6-Induction in 1,2-Additions to Acylsilanes

Sandra Gassmann; Boris Guintchin; Stefan Bienz

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New Silicon Groups as Potential Chiral Auxiliaries. Synthesis and Highly Selective Chiral 1,6-Induction in 1,2-Additions to Acylsilanes

机译：新的硅基作为潜在的手性助剂。酰基硅烷的1,2-加成中的合成和高选择性手性1,6-诱导

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Chiral silicon groups possessing an asymmetric and chelating alkoxymethyl substituent at silicon have been prepared, and it was that these groups may have substitantial utility as stereodirecting auxiliaries. For the 1,2-addition of organometallic species to chiral acylsilanes, auxiliaries with a single stereogenic center at position 6 with respect to the reactive carbonyl C atom proved particularly valuable. Compounds with such auxiliaries are earily accessible in enantiomerically pure form, and the chiral groups induce #pi#-facial selectivities of as high as 98:2. In an example it is shown that chiral 1,6-induction may dominate over 1,5-induction.

机译：已经制备了在硅上具有不对称和螯合的烷氧基甲基取代基的手性硅基团，并且这些基团可以作为立体定向助剂具有替代性的效用。对于将有机金属物质与手性酰基硅烷进行1，2-加成，相对于活性羰基C原子在位置6处具有单个立体中心的助剂被证明特别有价值。具有这类助剂的化合物可以以对映体纯净的形式容易地获得，并且手性基团诱导高达98：2的＃pi＃面部选择性。在一个实例中，显示了手性1，6-诱导可以主导于1，5-诱导。

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《Organometallics》 |2001年第9期|共11页
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Sandra Gassmann; Boris Guintchin; Stefan Bienz;
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中图分类有机化学;有机质材料;
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1. New Silicon Groups as Potential Chiral Auxiliaries. Synthesis and Highly Selective Chiral 1,6-Induction in 1,2-Additions to Acylsilanes [J] . Sandra Gassmann, Boris Guintchin, Stefan Bienz Organometallics . 2001,第9期

机译：新的硅基作为潜在的手性助剂。酰基硅烷的1,2-加成中的合成和高选择性手性1,6-诱导
2. Gold(I)-catalyzed asymmetric induction of planar chirality by intramolecular nucleophilic addition to chromium-complexed alkynylarenes: Asymmetric synthesis of planar chiral (1H-isochromene and 1,2- dihydroisoquinoline)chromium complexes [J] . Murai M., Sota Y., Onohara Y., The Journal of Organic Chemistry . 2013,第21期

机译：金（I）催化的分子内亲核加成铬复杂的炔芳烃的平面手性的不对称诱导：平面手性（1H-异戊二烯和1,2-二氢异喹啉）铬配合物的不对称合成
3. Asymmetric Synthesis of Chiral Amines by Highly diastereoselective 1,2-Additions of Organometallic Reagents to N-tert-Butanesulfinyl Imines [J] . Derek A. Cogan, Guangcheng Liu, Jonathan Ellman Tetrahedron . 1999,第29期

机译：有机金属试剂对N-叔丁亚磺酰基亚胺的高度非对映选择性1,2-加成反应不对称合成手性胺
4. Rhodium-Catalyzed Asymmetric 1,6-Addition of Aryltitanates to 1,3-Enynyl Ketones.Catalytic Asymmetric Synthesis of Axially Chiral Allenes [C] . Norihito Tokunaga, Kazuya Inoue, Tamio Hayashi Symposium on Organometallic Chemistry . 2003

机译：铑催化的不对称1,6-加入芳基酸酯至1,3-烯基酮。催化不对称合成轴向手性血症
5. Synthesis of cis,cis-6-aminospiro[4.4]nonan-1-ol and application of its derivatives as chiral ligands and auxiliaries. [D] . Lait, Susan M. 2004

机译：顺式，顺式-6-氨基螺[4.4]壬基-1-醇的合成及其衍生物作为手性配体和助剂的应用。
6. Synthesis of Chiral Enantiopure Zirconocene Imido Complexes: Highly Selective Kinetic Resolution and Stereoinversion of Allenes and Evidence for a Stepwise Cycloaddition/Retrocycloaddition Reaction Mechanism [O] . Zachary K. Sweeney, Jennifer L. Salsman, Richard A. Andersen, -1

机译：手性对映体纯的锆茂亚胺配合物的合成：丙二烯的高选择性动力学拆分和立体转化以及循序环加成/逆环加成反应机理的证据
7. Enantioselective Synthesis of Chiral Propargylic Silanes by Copper-Catalyzed 1,4-Selective Addition of Silicon Nucleophiles to Enyne-Type ,,,-Unsaturated Acceptors [O] . -1

机译：通过铜催化的1,4选择性加入硅亲核试剂对enyne型,,, - 不饱和的受体的致注重丙氨酸硅烷合成
8. Chiral Synthesis via Organoboranes. 18. Selective Reductions. 43. Diisopinocampheylchloroborane as an Excellent Chiral Reducing Reagent for the Synthesis of Halo Alcohols of High Enantiomeric Purity. A Highly Enantioselective Synt [R] . Srebnik, M., Ramachandran, P. V., Brown, H. C. 1988

机译：有机硼烷的手性合成。 18.选择性削减。 43. Diisopinocampheylchloroborane作为一种优良的手性还原剂，用于合成高对映体纯度的卤代醇。高度对映选择性合成

New Silicon Groups as Potential Chiral Auxiliaries. Synthesis and Highly Selective Chiral 1,6-Induction in 1,2-Additions to Acylsilanes

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