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

Ulrich Groth | Zendy; Marc Jung | Zendy; Till Vogel | Zendy

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

Author(s) -

Ulrich Groth,

Marc Jung,

Till Vogel

Publication year - 2004

Publication title -

synlett

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.712

H-Index - 133

eISSN - 1437-2096

pISSN - 0936-5214

DOI - 10.1055/s-2004-822895

Subject(s) - chemistry , methylene , diastereomer , intramolecular force , pinacol , catalysis , chromium , ring (chemistry) , medicinal chemistry , scavenger , manganese , ring size , organic chemistry , polymer chemistry , radical

Using only 10% of CrCl 2 as catalyst, manganese-powder as reducing agent and TMSCl as scavenger, 2-methylene-α,ω-di-aldehydes 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.

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