Intramolecular Chromium(II)-Catalyzed Pinacol Cross Coupling of 2-Methylene-α,ω-dicarbonyls

Intramolecular Chromium(II)-Catalyzed Pinacol Cross Coupling of 2-Methylene-α,ω-dicarbonyls

Abstract Using only 10% of CrCl 2 as catalyst, manganese-powder as reducing agent and TMSCl as scavenger, 2-methylene-α,ω-di­aldehydes and -ketones can be coupled to form cyclic diols dia­stereoselectively. The diastereomeric excess strongly depends on the ring size and the substituents of the ω-car...

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Veröffentlicht in:Synlett 2004-05, Vol.2004 (6), p.1054-1058
Hauptverfasser: Groth, Ulrich, Jung, Marc, Vogel, Till
Format: Artikel
Sprache:eng
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Zusammenfassung:Abstract Using only 10% of CrCl 2 as catalyst, manganese-powder as reducing agent and TMSCl as scavenger, 2-methylene-α,ω-di­aldehydes and -ketones can be coupled to form cyclic diols dia­stereoselectively. The diastereomeric excess strongly depends on the ring size and the substituents of the ω-carbonyl group. The greater the ring size the higher diastereoselectivities are observed. In all cases CIS-diols are preferentially formed.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-2004-822895