19028-68-3Relevant academic research and scientific papers
Chemo- and Enantioselective Acyl Transfers by Lipases and Acylase I: Preparative Applications in Hydroxymethylpiperidine Chemistry
Lundell, Katri,Lehtinen, Petka,Kanerva, Liisa T.
, p. 790 - 796 (2003)
The lipase- and acylase I-catalysed acylation of bifunctional 2- and 3-hydroxymethylpiperidines (1 and 2) and the alcoholysis of the corresponding diacylated counterparts 7 and 8 have been studied. Lipase AK from Pseudomonas fluorescens allowed the preparative-scale resolution of 7 in neat butanol at 50% conversion whereas the 3-regioisomer 8 reacted with negligible enantioselectivity (E = 7). The lipase- and acylase I-catalysed acylations of 1 and 2 in organic solvents proceeded with low enantioselectivity. On the other hand, more than 90% of 1 and 2 were transformed to amino esters 3 and 4, respectively, in a highly chemoselective O-acylation with 2,2,2-trifluoroethyl butanoate in the presence of Candida antarctica lipase A in TBME. The O-protected product 3 in the reaction mixture was readily available to another transformation at the piperidine nitrogen although 3 was not separated due to intramolecular O→N acyl migration. The tendency for acyl migration was much less significant in the case of 4.
