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Synthesis 2000; 2000(7): 914-916
DOI: 10.1055/s-2000-6293
short paper
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Application of the Molybdenum-Catalysed Hydrostannation Towards a Flexible Synthesis of Substituted Unsaturated Amino Acids

Uli Kazmaier* , Dagmar Schauß, Matthias Pohlman, Stefan Raddatz
  • *Organisch-Chemisches Institut der Universität, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany; Fax +49(6221)544205; E-mail: ck1@popix.urz.uni-heidelberg.de
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Publication Date:
31 December 2000 (online)

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Application of the molybdenum catalysed hydrostannation towards propargylic esters of amino acids allows for the regioselective synthesis of α-stannylated allylic esters, suitable substrates for chelate Claisen rearrangements. α-Stannylated allylic carbonates can be subjected to palladium catalysed allylic alkylations using chelated amino acid ester enolates as nucleophiles. The stannylated amino acids obtained can be further modified via cross-coupling reactions.

allylic alkylation - Claisen rearrangement - cross coupling - hydrostannation - molybdenum