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Intramolecular chromium(II)-catalyzed pinacol cross coupling of 2-methylene-α,ω-dicarbonyls
Groth, Ulrich,Jung, Marc,Vogel, Till
, p. 1054 - 1058 (2004)
Using only 10% of CrCl2 as catalyst, manganese-powder as reducing agent and TMSC1 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.
