Zhou Aihua, Hanson Paul R
Department of Chemistry, University of Kansas, Lawrence, Kansas 66045-7582, USA.
Org Lett. 2008 Jul 17;10(14):2951-4. doi: 10.1021/ol8009072. Epub 2008 Jun 14.
A divergent synthetic approach to new sultams utilizing intramolecular oxa-Michael and Baylis-Hillman reactions of readily prepared vinyl sulfonamides and suitably protected amino alcohols, is reported. A variety of seven- and eight-membered ring sultam scaffolds were synthesized using oxa-Michael pathways, whereas both five- and six-membered rings were synthesized using Baylis-Hillman methods. Baylis-Hillman reactions proceed with good to excellent levels of diastereoselectivity, and oxa-Michael reactions leading to eight-membered ring sultams provide empirical evidence validating 8- endo-trig cyclization pathways.
报道了一种利用易于制备的乙烯基磺酰胺和适当保护的氨基醇的分子内氧杂-Michael反应和Baylis-Hillman反应来合成新型磺内酰胺的发散性合成方法。使用氧杂-Michael途径合成了各种七元环和八元环磺内酰胺支架,而五元环和六元环则使用Baylis-Hillman方法合成。Baylis-Hillman反应具有良好到优异的非对映选择性,生成八元环磺内酰胺的氧杂-Michael反应提供了验证8-endo-trig环化途径的实验证据。