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Synthesis of 3‐ and 4‐Hydroxy‐2‐aminocyclohexanecarboxylic Acids by Iodocyclization
Author(s) -
Szakonyi Zsolt,
Gyónfalvi Szilvia,
Forró Enikö,
Hetényi Anasztázia,
De Kimpe Norbert,
Fülöp Ferenc
Publication year - 2005
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.200500297
Subject(s) - chemistry , enantiomer , amino acid , stereochemistry , transformation (genetics) , lactam , catalysis , combinatorial chemistry , organic chemistry , biochemistry , gene
Starting from cis ‐7‐azabicyclo[4.2.0]oct‐4‐en‐8‐one, novel routes have been developed for the synthesis of 2‐amino‐4‐hydroxycyclohexanecarboxylic acid and its 3‐hydroxy‐substituted analog via iodooxazine, iodooxazoline or iodolactone intermediates. After CAL‐B‐catalyzed enzymatic transformation of the starting β‐lactam, the iodolactone method was applied to the synthesis of 3‐hydroxy‐substituted β‐amino acid enantiomers. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)