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

Journal of Organic Chemistry 2014
Martins Priede, Mihail Kazak, Toms Kalnins, Kirill Shubin, Edgars Sūna

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 α-hydroxymethyl ketimines undergo highly diastereoselective reduction to syn- or anti-1,3-amino alcohols.

Keywords
Formaldehyde; Lithium Diastereo-selectivity; Diastereoselective; Diastereoselective reduction; Enamides; Hydroxymethylation; Ketimines
DOI
10.1021/jo500506u
Hyperlink
http://pubs.acs.org/doi/abs/10.1021/jo500506u

Priede, M., Kazak, M., Kalnins, T., Shubin, K., Sūna, E. Diastereoselective Hydroxymethylation of Cyclic N-tert-Butanesulfinylketimines Using Methoxymethanol as Formaldehyde Source. Journal of Organic Chemistry, 2014, Vol.79, No.8, pp.3715-3724. ISSN 0022-3263. e-ISSN 1520-6904. Available from: doi:10.1021/jo500506u

Publication language
English (en)