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A Straightforward Approach towards Isoxazoline Amino Acid Esters by Domino Michael Additions/Nitrile Oxide Cycloadditions
Author(s) -
Wirtz Lisa,
Kazmaier Uli
Publication year - 2011
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.201100233
Subject(s) - nitrile , nitroalkene , chemistry , alkene , cycloaddition , michael reaction , domino , organic chemistry , amino acid , nitronate , oxide , combinatorial chemistry , enantioselective synthesis , catalysis , nitro , biochemistry , alkyl
The syntheses of new heterocyclic isoxazoline amino acids are described based on a domino Michael addition/nitrile oxide formation/[3+2] cycloaddition approach. Chelated amino acid ester enolates can be added to nitroalkenes, and the generated nitronates are directly converted into nitrile oxides. These can be trapped intramolecularly by an alkene as a dipolarophile. The alkene can be introduced either via the nitroalkene or via the chelated enolate. Therefore, different types of heterocyclic amino acids can be obtained in a simple one‐pot protocol.