Enantioselective glyoxylate-ene reactions catalysed by (salen)chromium(III) complexes

An enantioselective carbonyl-ene reaction of alkyl glyoxylates with various 1,1-disubstituted olefins, catalysed by chiral (salen)Cr(III)BF4 complexes, has been studied. We found that a chromium complex bearing adamantyl substituents at the 3,3′-positions of the salicylidene moiety catalysed the reaction with much greater selectively than the classic Jacobsen-type catalyst. The reaction proceeded effectively under undemanding conditions in the presence of 2 mol % of the catalyst in an acceptable yield and with 59-92% ee.