title: Diastereoselective hydroxymethylation of cyclic N-tert-butanesulfinylketimines using methoxymethanol as formaldehyde source.
abstract: 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.
authors.affiliation: Latvian Institute of Organic Synthesis , Aizkraukles 21, LV-1006, Riga, Latvia.
authors.forename: Martins
authors.initials: M
authors.lastname: Priede
authors.forename: Mihail
authors.initials: M
authors.lastname: Kazak
authors.forename: Toms
authors.initials: T
authors.lastname: Kalnins
authors.forename: Kirill
authors.initials: K
authors.lastname: Shubin
authors.forename: Edgars
authors.initials: E
authors.lastname: Suna
mesh_terms: D000605:Amino Alcohols / Q000737:chemistry*; D005557:Formaldehyde / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D008745:Methylation; D015394:Molecular Structure; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000737:chemistry*
chemical_list: D000605:Amino Alcohols; D007097:Imines; D013438:Sulfhydryl Compounds; D005557:Formaldehyde