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‘N‐Stereogenic Quaternary Ammonium Salts’ from L ‐Amino Acids: Synthesis, Separation, and Absolute Configuration
Author(s) -
Wu HuaFang,
Lin WenBin,
Xia LiZi,
Luo YingGang,
Chen XiaoZhen,
Li GuoYou,
Zhang GuoLin,
Pan XinFu
Publication year - 2009
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200800326
Subject(s) - stereocenter , chemistry , diastereomer , absolute configuration , ammonium , amino acid , stereochemistry , organic chemistry , enantioselective synthesis , catalysis , biochemistry
Diastereoisomeric linear and cyclic ‘N‐chiral quaternary ammonium salts’ (QASs) were efficiently synthesized from corresponding L ‐amino acids in high yields. The diastereoisomers of each pair of ‘N‐chiral QASs’ were successfully separated. The absolute configurations of these QASs were determined predominately by X‐ray single‐crystal analysis. The 1 H‐NMR data of ‘N‐chiral QASs’ provided characteristic information on the configuration of the N‐chiral center. ‘N‐Chiral QASs’ exemplified by [ N ( R )]‐ 2a and [ N ( S )]‐ 2a are stable in protic and aprotic solvents within a broad pH and temperature range.