一种用于合成1,5-顺式-(E)-二醇的双烯丙基硼化试剂的开发：应用于四纤维蛋白C(23)-C(40)片段的合成。
Development of a Double Allylboration Reagent Targeting 1,5-syn-(E)-Diols: Application to the Synthesis of the C(23)-C(40) Fragment of Tetrafibricin.
作者信息
Nuhant Philippe, Kister Jeremy, Lira Ricardo, Sorg Achim, Roush William R
机构信息
Departments of Chemistry, The Scripps Research Institute, Florida, 130 Scripps Way, Jupiter, FL 33458, USA.
出版信息
Tetrahedron. 2011 Sep 2;67(35):6497-6512. doi: 10.1016/j.tet.2011.06.008.
Abstract
Interest in the synthesis of the C(23)-C(40) fragment 2 of tetrafibricin prompted us to develop a new method for the synthesis of 1,5-syn-(E)-diols. Toward this end, the kinetically controlled hydroboration of allenes 6, 33, ent-39, 42 and 45 with the Soderquist borane 25R were studied. Tetrabutylammonium allenyltrifluoroborate 45 gave superior results and was utilized in a double allylboration sequence with two different aldehydes to provide the targeted 1,5-syn-(E)-diols in generally high yields (72-98%), and with high enantioselectivity (>95% e.e.), diastereoselectivity (d.r. >20:1), and (E)/(Z) selectivity (>20:1). This new method was applied to the synthesis of the C(23)-C(40) fragment 2 of tetrafibricin.
摘要
对纤维四糖素C(23)-C(40)片段2合成的兴趣促使我们开发一种合成1,5-顺式-(E)-二醇的新方法。为此，研究了用索德奎斯特硼烷25R对丙二烯6、33、对映-39、42和45进行动力学控制的硼氢化反应。四丁基铵烯丙基三氟硼酸盐45给出了更好的结果，并用于与两种不同的醛进行双烯丙基硼化反应序列，以通常高的产率(72-98%)、高对映选择性(>95% ee)、非对映选择性(d.r.>20:1)和(E)/(Z)选择性(>20:1)提供目标1,5-顺式-(E)-二醇。这种新方法被应用于纤维四糖素C(23)-C(40)片段2的合成。
相似文献
1
Development of a Double Allylboration Reagent Targeting 1,5-syn-(E)-Diols: Application to the Synthesis of the C(23)-C(40) Fragment of Tetrafibricin.一种用于合成1,5-顺式-(E)-二醇的双烯丙基硼化试剂的开发：应用于四纤维蛋白C(23)-C(40)片段的合成。
Tetrahedron. 2011 Sep 2;67(35):6497-6512. doi: 10.1016/j.tet.2011.06.008.
2
Enantio- and diastereoselective synthesis of (E)-1,5-syn-diols: application to the synthesis of the C(23)-C(40) fragment of tetrafibricin.对映选择性和非对映选择性合成（E）-1,5-顺式二醇：在四纤维菌素 C(23)-C(40)片段合成中的应用。
Org Lett. 2011 Apr 1;13(7):1868-71. doi: 10.1021/ol2003836. Epub 2011 Mar 4.
3
Enantioselective synthesis of 1,5-anti- and 1,5-syn-diols using a highly diastereoselective one-pot double allylboration reaction sequence.使用高度非对映选择性的一锅法双烯丙基硼化反应序列对1,5-反式二醇和1,5-顺式二醇进行对映选择性合成。
J Am Chem Soc. 2002 Nov 20;124(46):13644-5. doi: 10.1021/ja028055j.
4
Stereoselective synthesis of gamma-substituted (Z)-allylic boranes via kinetically controlled hydroboration of allenes with 10-TMS-9-borabicyclo[3.3.2]decane.通过丙二烯与10-三甲基硅基-9-硼双环[3.3.2]癸烷的动力学控制硼氢化反应立体选择性合成γ-取代的(Z)-烯丙基硼烷。
J Am Chem Soc. 2009 Oct 14;131(40):14174-5. doi: 10.1021/ja905494c.
5
Enantioselective synthesis of (Z)- and (E)-2-methyl-1,5-anti-pentenediols via an allene hydroboration-double-allylboration reaction sequence.通过丙二烯硼氢化-双烯丙基硼氢化反应序列对（Z）-和（E）-2-甲基-1,5-反戊二烯二醇进行对映选择性合成。
J Am Chem Soc. 2013 Jun 26;135(25):9512-7. doi: 10.1021/ja4033633. Epub 2013 Jun 12.
6
Enantioselective synthesis of 2-methyl-1,2-syn- and 2-methyl-1,2-anti-3-butenediols via allene hydroboration-aldehyde allylboration reaction sequences.通过丙二烯硼氢化-醛烯丙基硼化反应序列对映选择性合成 2-甲基-1,2-顺式和 2-甲基-1,2-反式-3-丁二烯二醇。
J Am Chem Soc. 2009 Oct 21;131(41):14602-3. doi: 10.1021/ja904599h.
7
Diastereo- and enantioselective synthesis of (E)-2-Methyl-1,2-syn- and (E)-2-Methyl-1,2-anti-3-pentenediols via allenylboronate kinetic resolution with ((d)Ipc)2BH and aldehyde allylboration.通过烯丙基硼酸酯动力学拆分与((d)Ipc)2BH 和醛烯丙基硼化反应，对映选择性和非对映选择性合成（E）-2-甲基-1,2-顺式和（E）-2-甲基-1,2-反式-3-戊二烯二醇。
Org Lett. 2012 Jun 15;14(12):3028-31. doi: 10.1021/ol3010968. Epub 2012 May 30.
8
Development of α-Borylmethyl-()-crotylboronate Reagent and Enantioselective Syntheses of ()-δ-Hydroxymethyl--homoallylic Alcohols via Highly Stereoselective Allylboration.α-硼代甲基-()-巴豆基硼酸酯试剂的开发及通过高立体选择性烯丙基硼化反应对 ()-δ-羟甲基--高烯丙醇的对映选择性合成。
Org Lett. 2021 Dec 17;23(24):9451-9456. doi: 10.1021/acs.orglett.1c03628. Epub 2021 Dec 3.
9
Stereoselective synthesis of syn,syn- and syn,anti-1,3,5-triols via intramolecular hydrosilylation of substituted pent-3-en-1,5-diols.通过取代的戊-3-烯-1,5-二醇的分子内硅氢化反应立体选择性合成顺式、顺式-和顺式、反式-1,3,5-三醇。
Org Lett. 2009 Jul 2;11(13):2932-5. doi: 10.1021/ol9009877.
10
Enantio- and Diastereoselective Synthesis of 1,5-syn-(Z)-Amino Alcohols via Imine Double Allylboration: Synthesis of trans-1,2,3,6-Tetrahydropyridines and Total Synthesis of Andrachcine.通过亚胺双烯丙基硼化反应对映选择性和非对映选择性合成 1,5-顺式-(Z)-氨基醇：反式-1,2,3,6-四氢吡啶的合成和安那屈嗪的全合成。
Org Lett. 2017 May 19;19(10):2646-2649. doi: 10.1021/acs.orglett.7b00995. Epub 2017 May 4.
引用本文的文献
1
Enantio- and diastereoselective synthesis of syn-β-hydroxy-α-vinyl carboxylic esters via reductive aldol reactions of ethyl allenecarboxylate with 10-TMS-9-Borabicyclo[3.3.2]decane and DFT analysis of the hydroboration pathway.通过乙基丙炔酸酯与 10-TMS-9-硼双环[3.3.2]癸烷的还原醛醇缩合反应，对映选择性和非对映选择性合成顺-β-羟基-α-乙烯基羧酸酯，以及硼氢化途径的 DFT 分析。
Org Lett. 2013 Nov 1;15(21):5436-9. doi: 10.1021/ol4025277. Epub 2013 Oct 18.
2
(Diisopinocampheyl)borane-mediated reductive aldol reactions of acrylate esters: enantioselective synthesis of anti-aldols.(二异松蒎基)硼烷促进的丙烯酸酯酯的还原Aldol 反应：反式Aldol 的对映选择性合成。
Org Lett. 2013 Aug 2;15(15):3922-5. doi: 10.1021/ol401679g. Epub 2013 Jul 25.
3
Diisopinocampheylborane-mediated reductive aldol reactions: highly enantio- and diastereoselective synthesis of syn aldols from N-acryloylmorpholine.二异松蒎基硼烷介导的还原Aldol 反应：N-丙烯酰吗啉的高对映选择性和非对映选择性合成顺式Aldol 产物。
Angew Chem Int Ed Engl. 2013 Aug 12;52(33):8703-7. doi: 10.1002/anie.201302535. Epub 2013 Jul 1.
4
Enantio- and diastereoselective synthesis of N-acetyl dihydrotetrafibricin methyl ester.对映选择性和非对映选择性合成 N-乙酰二氢四呋辛甲酯。
J Am Chem Soc. 2013 Apr 10;135(14):5340-3. doi: 10.1021/ja401918r. Epub 2013 Mar 26.
5
Diastereo- and enantioselective synthesis of (E)-2-Methyl-1,2-syn- and (E)-2-Methyl-1,2-anti-3-pentenediols via allenylboronate kinetic resolution with ((d)Ipc)2BH and aldehyde allylboration.通过烯丙基硼酸酯动力学拆分与((d)Ipc)2BH 和醛烯丙基硼化反应，对映选择性和非对映选择性合成（E）-2-甲基-1,2-顺式和（E）-2-甲基-1,2-反式-3-戊二烯二醇。
Org Lett. 2012 Jun 15;14(12):3028-31. doi: 10.1021/ol3010968. Epub 2012 May 30.
本文引用的文献
1
Synthesis of C1-C20 and C21-C40 fragments of tetrafibricin.四纤维丝菌素C1 - C20及C21 - C40片段的合成
Tetrahedron Lett. 2011 Apr 27;52(17):2254-2257. doi: 10.1016/j.tetlet.2011.01.086.
2
C(21)-C(40) of tetrafibricin via metal catalysis: beyond stoichiometric chiral reagents, auxiliaries, and premetalated nucleophiles.通过金属催化实现四肤菌素 C(21)-C(40)的构建：超越化学计量手性试剂、辅助试剂和预金属化亲核试剂。
Org Lett. 2011 May 6;13(9):2484-7. doi: 10.1021/ol200735r. Epub 2011 Apr 6.
3
Enantio- and diastereoselective synthesis of (E)-1,5-syn-diols: application to the synthesis of the C(23)-C(40) fragment of tetrafibricin.对映选择性和非对映选择性合成（E）-1,5-顺式二醇：在四纤维菌素 C(23)-C(40)片段合成中的应用。
Org Lett. 2011 Apr 1;13(7):1868-71. doi: 10.1021/ol2003836. Epub 2011 Mar 4.
4
Versatile configuration-encoded strategy for rapid synthesis of 1,5-polyol stereoisomers.多功能构象编码策略用于快速合成 1,5-聚醇立体异构体。
Org Lett. 2010 Nov 5;12(21):5016-9. doi: 10.1021/ol1021417.
5
Fluorous Mixture Synthesis of Four Stereoisomers of the C21-C40 Fragment of Tetrafibricin.四纤维丝菌素C21 - C40片段四种立体异构体的氟代混合物合成
Synlett. 2010 Mar 1;2010(4):667-674. doi: 10.1055/s-0029-1219376.
6
SULFANYLATION OF 1,3-DITHIANE ANIONS BY 5-(ALKYLSULFANYL)-1-PHENYLTETRAZOLES.5-（烷基硫烷基）-1-苯基四氮唑对1,3-二噻烷阴离子的硫烷基化反应
Collect Czechoslov Chem Commun. 2009 Jun 1;74(5):7711-7783. doi: 10.1135/cccc2008195.
7
Highly (E)-selective BF(3).Et(2)O-promoted allylboration of chiral nonracemic alpha-substituted allylboronates and analysis of the origin of stereocontrol.高对映选择性的 BF(3).Et(2)O 促进的手性非外消旋的 α-取代烯丙基硼酸酯的烯丙基硼化反应及立体控制起源分析。
Org Lett. 2010 Jun 18;12(12):2706-9. doi: 10.1021/ol1007444.
8
Origin of thermodynamic versus kinetic control of allene hydroboration with 9-borabicyclo[3.3.1]nonane and 10(R)-trimethylsilyl-9-borabicyclo[3.3.2]decane.热力学控制与动力学控制对 9-硼双环[3.3.1]壬烷和 10(R)-三甲基硅基-9-硼双环[3.3.2]癸烷对烯丙基硼氢化的影响。
Org Lett. 2009 Dec 3;11(23):5538-41. doi: 10.1021/ol902364d.
9
Enantioselective synthesis of 2-methyl-1,2-syn- and 2-methyl-1,2-anti-3-butenediols via allene hydroboration-aldehyde allylboration reaction sequences.通过丙二烯硼氢化-醛烯丙基硼化反应序列对映选择性合成 2-甲基-1,2-顺式和 2-甲基-1,2-反式-3-丁二烯二醇。
J Am Chem Soc. 2009 Oct 21;131(41):14602-3. doi: 10.1021/ja904599h.
10
Stereoselective synthesis of gamma-substituted (Z)-allylic boranes via kinetically controlled hydroboration of allenes with 10-TMS-9-borabicyclo[3.3.2]decane.通过丙二烯与10-三甲基硅基-9-硼双环[3.3.2]癸烷的动力学控制硼氢化反应立体选择性合成γ-取代的(Z)-烯丙基硼烷。
J Am Chem Soc. 2009 Oct 14;131(40):14174-5. doi: 10.1021/ja905494c.
Zotero 插件