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Synlett 1992; 1992(8): 633-635
DOI: 10.1055/s-1992-21437
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Acyclic Stereocontrol via Organogembismetallic Reagents; Part III1

Ilane Marek* , Jean-Michel Lefrançois, Jean-F. Normant
  • *Laboratoire de Chimie des Organo-Eléments, CNRS UA 473, Université P. et M. Curie, 4 Place Jussieu, F-75252 Paris Cedex 05, France
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Publication Date:
08 March 2002 (online)

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The metalla-Claisen reaction leads under very mild conditions, high chemical yields and diastereoselectivity to compounds with two adjacent asymmetric centers. For example, (Z)-1-heptenyllithium (2) was converted into (3S,4R)-3,4-dimethyl-1-nonene (5) by reaction with crotylmagnesium bromide and zinc(II) bromide and subsequent hydrolysis of the gem-1,1-bismetallic intermediate 4.