Tetrahedron Asymmetry p. 817 - 842 (1990)
Update date:2022-08-04
Topics:
Coote, Steven J.
Davies, Stephen G.
Goodfellow, Craig L.
Sutton, Kevin H.
Middlemiss, David
Naylor, Alan
(-)-(1S,2S)-(N,O-Dimethylephedrine)tricarbonylchromium(0) (6) and (-)-(1S,2R)-(N,O-dimethylpseudoephedrine)tricarbonylchromium(0) (22) undergo completely stereoselective ortho deprotonation upon treatment with alkyllithium base, followed by addition of an electrophile.In both cases, exclusive remolval of the pro-(R)-ortho proton was confirmed by single X-ray structure analyses of the methylated products.Addition of methyllithium onto the ortho-formylated derivative of complex (6) occurs stereoselectively, the stereochemistry of the major product being confirmed by a single crystal X-ray structure determination.The results presented demonstrate an efficient transfer of chirality from a side chain onto the (arene)tricarbonylchromium(0) complex and back to a different side chain.
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