N,O-Nucleosides from Ene Reaction of (Nitrosocarbonyl)mesitylene with Crotyl Alcohol: Selectivity, Scope, and Limitations
作者:Paolo Quadrelli、Serena Carosso、Misal Memeo、Bruna Bovio、Elena Valletta、Beatrice Macchi
DOI:10.1055/s-0036-1588695
日期:——
analogues through the Vorbrüggen protocol. The selectivity of the ene reaction is discussed in the light of C=C bond polarization and steric effects. The structures of the N,O-nucleosides are assigned and discussed on the basis of spectroscopic observations and X-ray analysis. The (nitrosocarbonyl)mesitylene intermediate undergoes an ene reaction with crotyl alcohol, affording two regioisomeric adducts in fair
摘要 (亚硝基羰基)1,3,5-三甲基苯中间体与巴豆醇进行烯反应,以合理的收率得到两种区域异构加合物。在空间上苛刻的(亚硝基羰基)亚甲基苯使C2 / Markovnikov方向略微移向C3 /反Markovnikov途径,从而提供了5-羟基异恶唑烷,可通过Vorbrüggen协议作为合成N,O-核苷类似物的合成子。根据C = C键的极化和空间效应,讨论了烯反应的选择性。N,O-核苷的结构是在光谱观察和X射线分析的基础上进行分配和讨论的。 (亚硝基羰基)1,3,5-三甲基苯中间体与巴豆醇进行烯反应,以合理的收率得到两种区域异构加合物。在空间上苛刻的(亚硝基羰基)亚甲基苯使C2 / Markovnikov方向略微移向C3 /反Markovnikov途径,从而提供了5-羟基异恶唑烷,可通过Vorbrüggen协议作为合成N,O-核苷类似物的合成子。根据C = C键的极化和空间效应,讨论了烯反应的