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A New Soluble Polymer‐Supported Sulfonyl Linker − Application to the Synthesis of Cyclic α‐Amino Acids
Author(s) -
Varray Stéphane,
Lazaro René,
Martinez Jean,
Lamaty Frédéric
Publication year - 2002
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 - 10.1002/1099-0690(200207)2002:14<2308::aid-ejoc2308>3.0.co;2-q
Subject(s) - chemistry , ethylene glycol , sulfonyl , metathesis , linker , cleavage (geology) , aromatization , amino acid , protecting group , organic chemistry , solid phase synthesis , polymer chemistry , combinatorial chemistry , polymer , polymerization , catalysis , biochemistry , alkyl , computer science , operating system , peptide , geotechnical engineering , fracture (geology) , engineering
Abstract A new soluble poly(ethylene glycol)‐supported protecting group of the SES (silylethylsulfonyl) type has been prepared and utilized in the synthesis of cyclic amino esters by ring‐closing metathesis (RCM). Acidic cleavage from the support was performed to recover the fully deprotected amino acids. More conventional deprotection conditions with fluoride anions resulted in aromatization of the heterocycles in the case of the 6‐membered ring and provided a new route to the synthesis of substituted pyridines. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).