Diastereoselective Hydroxymethylation of Cyclic N-tert-Butanesulfinylketimines Using Methoxymethanol as Formaldehyde Source

作者：Priede Martins; Kazak Mihail; Kalnins Toms; Shubin Kirill; Suna Edgars^*

来源：Journal of Organic Chemistry, 2014, 79(8): 3715-3724.

DOI：10.1021/jo500506u

Hydroxymethylation of cyclic tert-butanesulfinylketimine-derived lithium enamides with methoxymethanol proceeds with excellent diastereoselectivity (99:1 dr). Methoxymethanol is a stable and easy-to-handle source of anhydrous monomeric formaldehyde in the reaction with lithium enamides. Cyclic alpha-hydroxymethyl ketimines undergo highly diastereoselective reduction to syn- or anti-1,3-amino alcohols.

• 出版日期2014-4-18