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The use of O-methyl-N-(α-methylbenzyl)hydroxylamine as a novel chiral auxiliary in asymmetric ortho-deprotonation of the (η6-arene) chromium tricarbonyl complexes is described. Upon quenching of the resultant ortho-lithiated complex with an electrophile, 1,2-disubstituted (η6-arene) chromium tricarbonyl complexes were obtained in good yield and excellent levels of diastereoselectivity.
The use of the (S)-α-methylbenzyl group as a chiral auxiliary has allowed the diastereoselective ortho-deprotonation of a chromium tricarbonyl complexed phenoxy ring. When the resultant ortho-anion is treated with an aldehyde two diastereoisomeric complexes are formed, in relatively poor dr, which differ in the configuration of the newly formed benzylic stereogenic centre. However, both ortho-formylation...
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