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Synthesis of Potential Inhibitors of Ethylene Biosynthesis: The diastereoisomers of 1‐amino‐2‐bromocyclopropanecarboxylic acid
Author(s) -
Wick Lukas,
Tamm Christoph,
Boller Thomas
Publication year - 1995
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.19950780211
Subject(s) - diastereomer , chemistry , bromine , stereochemistry , amino acid , ethylene , organic chemistry , biochemistry , catalysis
Abstract The preparation of the diastereoisomers of 1‐amino‐2‐bromocyclopropanecarboxylic acid is described using the methyl (1 RS , 5 SR )‐2‐oxo‐3‐oxabicyclo[3.1.0]hexane‐1‐carboxylate 5 as starting material. The key step is the oxidation of 9 with subsequent radical introduction of bromine according to the Barton procedure. The 2‐bromo‐cyclopropanecarboxylates cis ‐ 11 and trans ‐ 11 were obtained as diastereoisomer mixture in a ratio of 3:1. They were converted into cis ‐ and trans ‐esters 12 and the acids 13 .