Palladium Catalyzed Asymmetric Allylation of 3-OBoc-Oxindoles: An Efficient Synthesis of 3-Allyl-3-hydroxyoxindoles

作者: Samydurai Jayakumar , Nandarapu Kumarswamyreddy , Muthuraj Prakash , Venkitasamy Kesavan

DOI: 10.1021/ACS.ORGLETT.5B00034

关键词:

摘要: 3-Allyl-3-hydroxyoxindoles were synthesized in very good enantio- (up to 97% ee) and diastereoselectivities (dr up 7.6:1) with contiguous quaternary tertiary stereogenic centers by employing tartrate derived bi(oxazoline) Pd-catalyzed allylation of 3-OBoc-oxindole. Synthetic utility 3-allyl-3-hydroxyoxindole was demonstrated synthesizing a highly substituted spiro(oxindole-3,2′-tetrahydrofuran) derivative yield stereoselectivity.

参考文章(45)
Samydurai Jayakumar, Subramaniam Muthusamy, Muthuraj Prakash, Venkitasamy Kesavan, Enantioselective Synthesis of Spirooxindole α‐exo‐Methylene‐γ‐butyrolactones from 3‐OBoc‐Oxindoles European Journal of Organic Chemistry. ,vol. 2014, pp. 1893- 1898 ,(2014) , 10.1002/EJOC.201301684
Allen Y. Hong, Brian M. Stoltz, The Construction of All-Carbon Quaternary Stereocenters by Use of Pd-Catalyzed Asymmetric Allylic Alkylation Reactions in Total Synthesis European Journal of Organic Chemistry. ,vol. 2013, pp. 2745- 2759 ,(2013) , 10.1002/EJOC.201201761
Nadine V. Hanhan, Nicolas R. Ball-Jones, Ngon T. Tran, Annaliese K. Franz, Catalytic Asymmetric [3+2] Annulation of Allylsilanes with Isatins: Synthesis of Spirooxindoles Angewandte Chemie. ,vol. 51, pp. 989- 992 ,(2012) , 10.1002/ANIE.201105739
Daisuke Sano, Kazuhiro Nagata, Takashi Itoh, Catalytic Asymmetric Hydroxylation of Oxindoles by Molecular Oxygen Using a Phase-Transfer Catalyst Organic Letters. ,vol. 10, pp. 1593- 1595 ,(2008) , 10.1021/OL800260R
Piyasena Hewawasam, Matthew Erway, Sandra L. Moon, Jay Knipe, Harvey Weiner, Christopher G. Boissard, Debra J. Post-Munson, Qi Gao, Stella Huang, Valentin K. Gribkoff, Nicholas A. Meanwell, Synthesis and structure-activity relationships of 3-aryloxindoles: a new class of calcium-dependent, large conductance potassium (maxi-K) channel openers with neuroprotective properties. Journal of Medicinal Chemistry. ,vol. 45, pp. 1487- 1499 ,(2002) , 10.1021/JM0101850
Michele Retini, Giulia Bergonzini, Paolo Melchiorre, Dioxindole in asymmetric catalytic synthesis: direct access to 3-substituted 3-hydroxy-2-oxindoles via 1,4-additions to nitroalkenes. Chemical Communications. ,vol. 48, pp. 3336- 3338 ,(2012) , 10.1039/C2CC30198A
V. Pratap Reddy Gajulapalli, Poopathy Vinayagam, Venkitasamy Kesavan, Organocatalytic asymmetric decarboxylative cyanomethylation of isatins using L-proline derived bifunctional thiourea. Organic and Biomolecular Chemistry. ,vol. 12, pp. 4186- 4191 ,(2014) , 10.1039/C4OB00271G
Zhong-Yan Cao, Yan Zhang, Cong-Bin Ji, Jian Zhou, A Hg(ClO4)2·3H2O Catalyzed Sakurai–Hosomi Allylation of Isatins and Isatin Ketoimines Using Allyltrimethylsilane Organic Letters. ,vol. 13, pp. 6398- 6401 ,(2011) , 10.1021/OL202705G
Bao-Dong Cui, Jian Zuo, Jian-Qiang Zhao, Ming-Qiang Zhou, Zhi-Jun Wu, Xiao-Mei Zhang, Wei-Cheng Yuan, Tandem Michael Addition–Ring Transformation Reactions of 3-Hydroxyoxindoles/3-Aminooxindoles with Olefinic Azlactones: Direct Access to Structurally Diverse Spirocyclic Oxindoles Journal of Organic Chemistry. ,vol. 79, pp. 5305- 5314 ,(2014) , 10.1021/JO500432C
Nubia Boechat, W. Kover, Vera Bongertz, Monica Bastos, Nelilma Romeiro, Maria Azevedo, Wagner Wollinger, Design, synthesis and pharmacological evaluation of HIV-1 reverse transcriptase inhibition of new indolin-2-ones. Medicinal Chemistry. ,vol. 3, pp. 533- 542 ,(2007) , 10.2174/157340607782360326