School of Chemical Science and Technology, Yunnan University, Kunming, Yunnan 650091, People's Republic of China.
Org Lett. 2022 Oct 28;24(42):7817-7821. doi: 10.1021/acs.orglett.2c03171. Epub 2022 Oct 19.
Hydroxymethylation of α-branched --butanesulfinyl ketimines with formaldehyde equivalents was developed to stereoselectively construct acyclic quaternary stereocenters bearing two sterically and electronically similar substituents. The stereoselective BuOK-promoted α-deprotonation of acyclic ketimines allowed for the stereodefined formation of fully substituted aza-enolates, followed by facially selective C-C bond formation involving formaldehyde formed , yielding α-hydroxymethylated products with precise stereocontrol.
发展了α-支链--丁烷亚磺酰基酮亚胺与甲醛等价物的羟甲基化反应，以立体选择性地构建具有两个空间位阻和电子相似取代基的非环状季立体中心。非环状酮亚胺的立体选择性 BuOK 促进的α-脱质子化作用允许全取代的氮杂烯醇盐的立体定义形成，然后是涉及形成的甲醛的面选择性 C-C 键形成，得到具有精确立体控制的α-羟甲基化产物。
