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Regioselective 2‐Imino‐1,3‐thiazolidine vs. 2‐Imino‐1,3‐oxazolidine Formation from the Vicinal sec ‐Amino Alcohol of Desosamine
Author(s) -
Ištuk Zorica Marušić,
Vujasinovi Ines,
Čikoš Ana,
Kragol Goran
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201300266
Subject(s) - chemistry , oxazolidine , vicinal , thiazolidine , regioselectivity , stereochemistry , alcohol , reagent , organic chemistry , catalysis
In order to optimize Mukaiyama reagent‐induced cyclization of vicinal sec ‐amino alcohols of desosamine origin towards exclusive formation of N′ ‐substituted‐2‐imino‐1,3‐thiazolidines via a thiocarbamoyl intermediate, the influence of reaction conditions was studied. A novel, mild, one‐pot, two‐step method was developed, and the formation of N′ ‐substituted‐2‐imino‐1,3‐oxazolidines as side products was minimized. The inversion of configuration at C‐2′ was unambiguously established using NMR‐based conformational analysis. A reaction mechanism was proposed. A test series of novel desosamine‐modified 14‐ and 15‐membered macrolides, bearing N′ ‐alkyl‐2‐imino‐1,3‐thiazolidines fused to the desosamine sugar were prepared.