Synthesis of Potential Inhibitors of Ethylene Biosynthesis: The diastereoisomers of 1‐amino‐2‐bromocyclopropanecarboxylic acid | Zendy

Wick Lukas | Zendy; Tamm Christoph | Zendy; Boller Thomas | Zendy

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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

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 .

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