Regio- and Chemoselective Formation of Spiroindolinone-Isoindolinone by a Palladium-Catalyzed Buchwald-Hartwig Addition-Elimination Sequence
作者： Himanshu H. Butani , Dipak D. Vachhani , Umed C. Bhoya , Anamik K. Shah , Erik V. Van der Eycken
关键词: Addition elimination 、 Chemistry 、 Catalysis 、 Sequence (biology) 、 Palladium 、 Organic chemistry 、 Isatin
摘要: The usual way to synthesize spiroindolinones is the application of isatin derivatives. Here, we report first Pd-catalyzed Buchwald–Hartwig addition–elimination strategy for formation spiroindolinone–isoindolinone architecture. Ugi-4-component reaction (Ugi-4CR) allows facile introduction diversity and increases practicality this protocol.
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sci-hub.se 参考文章(48)
Metal catalyzed cascade reactions Springer. ,(2006) , 10.1007/11603696
Luca Banfi, Andrea Basso, Renata Riva, Synthesis of Heterocycles Through Classical Ugi and Passerini Reactions Followed by Secondary Transformations Involving One or Two Additional Functional Groups Synthesis of Heterocycles via Multicomponent Reactions I. ,vol. 23, pp. 1- 39 ,(2010) , 10.1007/7081_2009_23
Eelco Ruijter, Rachel Scheffelaar, Romano V. A. Orru, Multicomponent Reaction Design in the Quest for Molecular Complexity and Diversity Angewandte Chemie. ,vol. 50, pp. 6234- 6246 ,(2011) , 10.1002/ANIE.201006515
Stefano Marcaccini, Tomás Torroba, The use of the Ugi four-component condensation Nature Protocols. ,vol. 2, pp. 632- 639 ,(2007) , 10.1038/NPROT.2007.71
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
Feng Zhou, Yun-Lin Liu, Jian Zhou, Catalytic Asymmetric Synthesis of Oxindoles Bearing a Tetrasubstituted Stereocenter at the C‐3 Position Advanced Synthesis & Catalysis. ,vol. 352, pp. 1381- 1407 ,(2010) , 10.1002/ADSC.201000161
Ponnusamy Shanmugam, Baby Viswambharan, Suchithra Madhavan, Synthesis of Novel Functionalized 3-Spiropyrrolizidine and 3-Spiropyrrolidine Oxindoles from Baylis−Hillman Adducts of Isatin and Heteroaldehydes with Azomethine Ylides via [3+2]-Cycloaddition Organic Letters. ,vol. 9, pp. 4095- 4098 ,(2007) , 10.1021/OL701533D
Hao Wu, Li-Li Zhang, Zhi-Qing Tian, Yao-Dong Huang, Yong-Mei Wang, Highly Efficient Enantioselective Construction of Bispirooxindoles Containing Three Stereocenters through an Organocatalytic Cascade Michael–Cyclization Reaction Chemistry: A European Journal. ,vol. 19, pp. 1747- 1753 ,(2013) , 10.1002/CHEM.201203221
Wangsheng Sun, Gongming Zhu, Chongyang Wu, Liang Hong, Rui Wang, “Organo–Metal” Synergistic Catalysis: The 1+1>2 Effect for the Construction of Spirocyclopentene Oxindoles Chemistry: A European Journal. ,vol. 18, pp. 13959- 13963 ,(2012) , 10.1002/CHEM.201201976
Christiane Marti, Erick M. Carreira, Construction of Spiro[pyrrolidine‐3,3′‐oxindoles] − Recent Applications to the Synthesis of Oxindole Alkaloids European Journal of Organic Chemistry. ,vol. 2003, pp. 2209- 2219 ,(2003) , 10.1002/EJOC.200300050