Direct Csp2-H Enolization: An Allenoate Alkylation Cascade Toward the Assembly of Multi-substituted Furans
作者： Debanjan Bakshi , Anand Singh
DOI: 10.1039/C7OB00248C
关键词:
摘要: A new disconnection toward tri- and tetrasubstituted furans has been conceptualized demonstrated. mild, base-mediated reaction of an allenoate pronucleophile with α-halo ketones/dicarbonyl compounds results in a Csp2-alkylation/enolization/O-vinylation sequence to ultimately afford substituted furan derivatives. The offers broad scope, provides facile access alkyl aryl furans, demonstrates the application allene functionality as two-carbon component construction furans.
rsc.org
sci-hub.se 参考文章(32)
Xin Cui, Xue Xu, Lukasz Wojtas, Martin M. Kim, X. Peter Zhang, Regioselective Synthesis of Multisubstituted Furans via Metalloradical Cyclization of Alkynes with α-Diazocarbonyls: Construction of Functionalized α-Oligofurans Journal of the American Chemical Society. ,vol. 134, pp. 19981- 19984 ,(2012) , 10.1021/JA309446N
Weibo Yang, A. Stephen K. Hashmi, Mechanistic insights into the gold chemistry of allenes Chemical Society Reviews. ,vol. 43, pp. 2941- 2955 ,(2014) , 10.1039/C3CS60441A
Jean Le Bras, Jacques Muzart, Palladium-catalysed inter- and intramolecular formation of C-O bonds from allenes. Chemical Society Reviews. ,vol. 43, pp. 3003- 3040 ,(2014) , 10.1039/C3CS60379B
Michael J. Krische, Cross-metathesis-based approaches to heteroaromatics: combining catalysts for furan formation. Proceedings of the National Academy of Sciences of the United States of America. ,vol. 107, pp. 3279- 3280 ,(2010) , 10.1073/PNAS.1000313107
Shengming Ma, Some Typical Advances in the Synthetic Applications of Allenes Chemical Reviews. ,vol. 105, pp. 2829- 2872 ,(2005) , 10.1021/CR020024J
Hun Young Kim, Seokwoo Lee, Sanghee Kim, Kyungsoo Oh, Regiodivergent halogenation of (E)-β-chlorovinyl ketones via soft α-vinyl enolization strategy. Organic Letters. ,vol. 17, pp. 450- 453 ,(2015) , 10.1021/OL5034354
Timothy J. Donohoe, John F. Bower, An expedient route to substituted furans via olefin cross-metathesis. Proceedings of the National Academy of Sciences of the United States of America. ,vol. 107, pp. 3373- 3376 ,(2010) , 10.1073/PNAS.0913466107
John F. Arnett, H. M. Walborsky, Vinyl anion. II Journal of Organic Chemistry. ,vol. 37, pp. 3678- 3683 ,(1972) , 10.1021/JO00796A024
Tohru Kambe, Toru Maruyama, Masayuki Nakano, Yoshiyuki Yamaura, Tomoyuki Shono, Akiteru Seki, Kiyoto Sakata, Takayuki Maruyama, Hisao Nakai, Masaaki Toda, Discovery of orally available 8-aza-5-thiaProstaglandin E1 analogs as highly selective EP4 agonists. Chemical & Pharmaceutical Bulletin. ,vol. 59, pp. 1523- 1534 ,(2011) , 10.1248/CPB.59.1523
Salvatore D. Lepore, Yuanjun He, Pamela Damisse, Studies on the base-promoted conversion of conjugated alkynyl esters to α-substituted α-allenyl esters Journal of Organic Chemistry. ,vol. 69, pp. 9171- 9175 ,(2004) , 10.1021/JO0487754