Highly Regio- and Diastereoselective Tethered Aza-Wacker Cyclizations of Alkenyl Phosphoramidates.
Highly Regio- and Diastereoselective Tethered Aza-Wacker Cyclizations of Alkenyl Phosphoramidates.
复制标题
DOI：
10.26434/chemrxiv.14132177.v1
复制
发表时间：
2021-03
期刊：
影响因子：
--
通讯作者：
Anand H Shinde;A. Thomas;J. Mague;Shyam Sathyamoorthi
中科院分区：
文献类型：
--
作者：
Anand H Shinde;A. Thomas;J. Mague;Shyam Sathyamoorthi
我们提出了高度非对映选择性的链烯基氨基磷酸酯的氮杂-瓦克环化反应。用5-氯-8-羟基喹啉“武装”氨基磷酸酯系链对于在这些反应中实现>20：1的非对映选择性是必要的。广泛探索了烯基醇和氨基磷酸酯系链的底物范围。证明了氧化环化的可扩展性，并且产物环磷酰胺被证明是有价值的合成子，包括用于脱链。用手性烯基前体，形成对映体纯的环状氨基磷酸酯。
We present highly diastereoselective tethered aza-Wacker cyclization reactions of alkenyl phosphoramidates. "Arming" the phosphoramidate tether with 5-chloro-8-quinolinol was essential to achieving >20:1 diastereoselectivity in these reactions. The substrate scope with respect to alkenyl alcohols and phosphoramidate tether was extensively explored. The scalability of the oxidative cyclization was demonstrated, and the product cyclophosphoramidates were shown to be valuable synthons, including for tether removal. With chiral alkenyl precursors, enantiopure cyclic phosphoramidates were formed.