(S)-(-)-2-(苯磺酰基)-3-苯基恶唑烷-3-醇对 - 丁烷亚磺酰亚胺的非对映选择性羟化（戴维斯恶唑烷）。
Diastereoselective Hydroxylation of --Butanesulfinyl Imines with 2-(Phenylsulfonyl)-3-phenyloxaziridine (Davis Oxaziridine).
机构信息
Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122, United States.
出版信息
Org Lett. 2022 Sep 16;24(36):6548-6553. doi: 10.1021/acs.orglett.2c02513. Epub 2022 Aug 31.
The diastereoselective α-hydroxylation of --butanesulfinyl metallodienenamine and metalloenamines with Davis oxaziridine affords α-hydroxy -sulfinyl imines with 50-88% yield and up to 98:2 diastereomeric ratio. Dramatic changes in diastereoselectivity and stereoselectivity were observed by choice of metal bases. The mechanistic understanding for the switch in diastereoselectivity was assisted by DFT computational modeling, which suggests the facial approach is governed by aza-enolate geometry. A one-pot protocol for the asymmetric synthesis of 1,2-amino alcohols is described.
--丁烷亚磺酰基金属二烯胺和金属烯胺的非对映选择性α-羟化作用与 Davis 恶唑烷反应，以 50-88%的收率和高达 98:2 的非对映体比率得到α-羟基-亚磺酰亚胺。通过选择金属碱，观察到非对映选择性和立体选择性的剧烈变化。通过密度泛函理论（DFT）计算模型的辅助，对非对映选择性转换的机理有了深入的了解，这表明面进攻受氮烯酸盐几何形状的控制。描述了一种用于手性合成 1,2-氨基醇的一锅法不对称合成方法。
Zotero 插件