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Synthesis 2009(14): 2435-2439
DOI: 10.1055/s-0029-1216862
DOI: 10.1055/s-0029-1216862
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of Highly Functionalized Proline Derivatives via a One-Pot Michael/SN′-Addition/Cyclization Approach
Weitere Informationen
Received
4 February 2009
Publikationsdatum:
02. Juni 2009 (online)
Publikationsverlauf
Publikationsdatum:
02. Juni 2009 (online)
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Abstract
Chelated enolates undergo Michael addition towards halogenated α,β-unsaturated esters in a highly stereoselective fashion. The enolates formed can be trapped with electrophiles such as Baylis-Hillman-type acrylates in a stereoselective fashion, before subsequent cyclization gives rise to substituted proline derivatives. Up to three stereogenic centers can be formed in this one-pot reaction.
Key words
amino acids - Baylis-Hillman - chelates - cyclization - Michael addition - one-pot reaction
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