Four-Component Assembly of Chiral N鈥揃 Heterocycles with a Natural Product-Like Framework

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• 作者：Francesco Montalbano ; Nuno R. Candeias ; Lu铆s F. Veiros ; V芒nia Andr茅 ; M. Teresa Duarte ; Maria R. Bronze ; Rui Moreira ; Pedro M. P. Gois
• 刊名：Organic Letters
• 出版年：2012
• 出版时间：February 17, 2012
• 年：2012
• 卷：14
• 期：4
• 页码：988-991
• 全文大小：328K
• 年卷期：v.14,no.4(February 17, 2012)
• ISSN：1523-7052

文摘

The dative N鈥揃 bond was used to simply assemble heterocycles with a skeleton akin to the 5-oxofuro[2,3-b]furan motif. Twenty-five new N鈥揃 heterocycles were prepared via a highly efficient one-pot four-component reaction in yields and diastereoselectivities up to 95% and >97%, respectively. Several reaction intermediates were discovered using electrospray ionization mass spectroscopy which set the basis for the mechanism elucidation using DFT calculations.