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Synlett 1990; 1990(10): 587-588
DOI: 10.1055/s-1990-21174
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Chiral Vinyl Anions for "Carbonyl Umpolung". Non-Chelate-Controlled Addition of an Enantiomerically Pure Vinyllithium Reagent to O-Protected 3-Hydroxybutyraldehydes

Manfred Braun* , Hellmut Mahler
  • *Institut für Organische Chemie und Makromolekulare Chemie der Universität Düsseldorf, Universitätsstrasse 1, D-4000 Düsseldorf, Federal Republic of Germany
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Publikationsdatum:
08. März 2002 (online)

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(2R,4R)-2,4-Dibenzyloxy-1-pentanol (7) is available by stereoselective reaction of the chiral vinyllithium reagent 1b ((R)-1-bromo-1-lithio-3-[(2-methoxyethoxy)methoxy]-1-butene) with (R)-3-benzyloxybutyraldehyde (2). Thus, the addition of a methanol-d1-synthon (-CH2OH) to O-protected 3-hydroxybutyraldehydes is possible in a "non-chelate-controlled" manner.