1,5-Asymmetric induction during nucleophilic additions to arenetricarbonylchromium complexes: tricarbonyl(eta(6)-1-methyl-4-{spiro[(1R,2S)-1,7,7-trimethylbicyclo[2.2.1]heptane-3,2'-1,3-dioxolan]-2-yloxy}benzene)chromium.

The tricarbonylchromium unit bound to the arene ring of the chiral title complex, [Cr(C(19)H(26)O(3))(CO)(3)], is rotated by ca 25 degrees in agreement with the proposed mechanism for 1,5-asymmetric induction of nucleophilic attack.

Vicinal stereocontrol during nucleophilic addition to arene chromium tricarbonyl complexes: formal synthesis of (+/-)-erythro Juvabione.

[reaction: see text] Vicinal stereocontrol during nucleophilic addition of tert-butyl lithiopropionate to eta(6)-anisole chromium tricarbonyl complexes with differing para substituents has been studied. Excellent vicinal double stereoinduction (>99:1) was observed when the para substituent was Si(CH(3))(3), and this has been applied to a stereoselective formal synthesis of (+/-)-erythro Juvabione. Asymmetric synthesis by chiral auxiliary directed nucleophilic addition is also discussed.