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A convenient method for library construction: Parallel synthesis of β‐amino ester and quinoline derivatives in liquid phase using Ln(OTf) 3 ‐catalyzed three‐component reactions
Author(s) -
Kobayashi Shu,
Komiyama Susumu,
Ishitani Haruro
Publication year - 1998
Publication title -
biotechnology and bioengineering
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.136
H-Index - 189
eISSN - 1097-0290
pISSN - 0006-3592
DOI - 10.1002/(sici)1097-0290(199824)61:1<23::aid-bit7>3.0.co;2-0
Subject(s) - quinoline , trifluoromethanesulfonate , silyl enol ether , chemistry , catalysis , aldehyde , lewis acid catalysis , lewis acids and bases , component (thermodynamics) , organic chemistry , silylation , lanthanide , combinatorial chemistry , ion , physics , thermodynamics
A convenient method for library construction in liquid phase, which is based on lanthanide triflate (Ln(OTf) 3 )‐catalyzed three‐component reactions, has been developed. Equimolar amounts of each component, an aldehyde, an amine, and a silyl enol ether or an alkene, react smoothly in the presence of Ln(OTf) 3 , and the work‐up and purification processes are performed by simply passing through a short column. The key is to use Ln(OTf) 3 as a Lewis acid catalyst, which is not decomposed during the work‐up and purification steps, and is easily separated from products by the simple procedure. According to this method, various high‐quality β‐amino ester and quinoline derivatives have been prepared in parallel in large quantities. © 1998 John Wiley & Sons, Inc. Biotechnol Bioeng (Comb Chem) 61:23–31, 1998.