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Org Biomol Chem
; 17(10): 2753-2758, 2019 03 06.
Article
in English
| MEDLINE
| ID: mdl-30785174
ABSTRACT
A system for the directed hydrogenation of nitrogen heterocycles is described in which hydrogen is delivered cis to a hydroxymethyl group by a rhodium catalyst with a simple phosphine ligand. The chemistry is applied to the synthesis of the hygric acid moiety of lincomycin and the pipecolic acid moiety of Argatroban. A series of control experiments indicate that the stereoselectivity is a result of a combination of both coordination and hydrogen bonding.