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Synlett 1991; 1991(3): 179-180
DOI: 10.1055/s-1991-20670
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Diastereoselective Additions of Lithiated Methoxyallene Towards Chiral Aldehydes

Stephan Hormuth* , Hans-Ulrich Reissig
  • *Institut für Organische Chemie der Technischen Hochschule Darmstadt, Petersenstraße 22, D-6100 Darmstadt, Germany
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Publikationsdatum:
07. März 2002 (online)

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Lithiated methoxyallene 1 (1-methoxy-1,2-propadienyl-lithium) adds with good to excellent anti-selectivity to chiral aldehydes. The reaction of 1 with 2-dibenzylaminoalkanals 5 gives 5-dibenzylamino-4-hydroxy-3-methoxy-1,2-alkadienes, which can easily be converted into enantiomerically pure furan derivatives like 7a, 8a, 9a, and 10a.