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Remote chirality transfer in nucleophilic catalysis with N ‐(4‐pyridinyl)‐ L ‐proline derivatives
Author(s) -
Kawabata Takeo,
Stragies Roland,
Fukaya Takayuki,
Fuji Kaoru
Publication year - 2002
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.10166
Subject(s) - chemistry , stereocenter , chirality (physics) , nucleophile , kinetic resolution , catalysis , pyridine , enantiomer , selectivity , stereochemistry , proline , enantioselective synthesis , organocatalysis , medicinal chemistry , combinatorial chemistry , amino acid , organic chemistry , biochemistry , chiral symmetry breaking , physics , quantum mechanics , quark , nambu–jona lasinio model
Chiral nucleophilic catalysts 5–15 were prepared starting from L ‐proline. Catalysts 9 and 14 promoted acylative kinetic resolution of racemic amino alcohol derivative 16 with selectivity factors of 8.1 and 11, respectively, at ambient temperature. Since chiral elements are not present in the catalytically active pyridine ring in these catalysts, chirality transfer from the remote stereogenic center to the reactive site ( N ‐acylpyridinium) is suggested to be responsible for the differentiation between enantiomers. Chirality 15:71–76, 2003. © 2002 Wiley‐Liss, Inc.