Vinylogous Mukaiyama-Michael Reactions of Dihydropyridinones.
作者： Hui Li , Jimmy Wu
DOI: 10.1021/ACS.ORGLETT.5B02778
关键词:
摘要: An In(III)-catalyzed vinylogous addition of O-silyl vinylketene acetals to 2,3-dihydro-4-pyridinones has been developed. The method features the unprecedented employment supersilyl groups influence γ versus α regiochemical control Mukaiyama–Michael (vM−Michael) reactions when γ-substituted are used. We also demonstrate that these allow facile access quinolizidine-based alkaloids such as deoxynupharidine and well lasubine I II.
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sci-hub.se 参考文章(61)
Hai-Hua Lu, Michael D. Martinez, Ryan A. Shenvi, An eight-step gram-scale synthesis of (−)-jiadifenolide Nature Chemistry. ,vol. 7, pp. 604- 607 ,(2015) , 10.1038/NCHEM.2283
Jeffrey T. Kuethe, Daniel L. Comins, Addition of metallo enolates to chiral 1-acylpyridinium salts: total synthesis of (+)-cannabisativine. Organic Letters. ,vol. 2, pp. 855- 857 ,(2000) , 10.1021/OL0056271
W. Stephen McCall, Teresa Abad Grillo, Daniel L. Comins, Stereoselective Synthesis of Acyclic Amino Alcohols via von Braun Ring Opening of Chiral Piperidines Organic Letters. ,vol. 10, pp. 3255- 3257 ,(2008) , 10.1021/OL801123X
Daniel Müller, Alexandre Alexakis, Copper-Catalyzed Asymmetric 1,4-Addition of Alkenyl Alanes to N-Substituted-2-3-dehydro-4-piperidones Organic Letters. ,vol. 14, pp. 1842- 1845 ,(2012) , 10.1021/OL3004436
Matthew B. Boxer, Hisashi Yamamoto, Tris(trimethylsilyl)silyl-Governed Aldehyde Cross-Aldol Cascade Reaction Journal of the American Chemical Society. ,vol. 128, pp. 48- 49 ,(2006) , 10.1021/JA054725K
Jiajing Tan, Matsujiro Akakura, Hisashi Yamamoto, The Supersilyl Group as a Carboxylic Acid Protecting Group: Application to Highly Stereoselective Aldol and Mannich Reactions Angewandte Chemie. ,vol. 52, pp. 7198- 7202 ,(2013) , 10.1002/ANIE.201300102
Jorma Hassfeld, Mathias Christmann, Markus Kalesse, Rapid Access to Polyketide Scaffolds via Vinylogous Mukaiyama Aldol Reactions Organic Letters. ,vol. 3, pp. 3561- 3564 ,(2001) , 10.1021/OL016677O
Qin Xu, Rui Zhang, Tao Zhang, Min Shi, Asymmetric 1,4-addition of arylboronic acids to 2,3-dihydro-4-pyridones catalyzed by axially chiral NHC-Pd(II) complexes. Journal of Organic Chemistry. ,vol. 75, pp. 3935- 3937 ,(2010) , 10.1021/JO1006224
Wesley J. Moran, Katharine M. Goodenough, Piotr Raubo, Joseph P. A. Harrity, A Concise Asymmetric Route to Nuphar Alkaloids. A Formal Synthesis of (−)-Deoxynupharidine Organic Letters. ,vol. 5, pp. 3427- 3429 ,(2003) , 10.1021/OL035156T
Masayuki Sato, Sakae Aoyagi, Seiji Yago, Chihiro Kibayashi, Lewis acid-promoted asymmetric conjugate allylation of N-acyl-2,3-dihydro-4-pyridones induced by intramolecular π interactions Tetrahedron Letters. ,vol. 37, pp. 9063- 9066 ,(1996) , 10.1016/S0040-4039(96)02129-6