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Catalytic asymmetric addition of diphenylzinc to cyclic alpha,beta-unsaturated ketones.

ABSTRACT: We have examined the use of our bis(sulfonamide) diol ligand (1) in the asymmetric addition of phenyl groups to cyclic alpha,beta-unsaturated ketones. Good to excellent enantioselectivities have been obtained with cyclic enones bearing alkyl substituents in the 2 position (71-97% enantiomeric excess). Furthermore, excellent enantioselectivities have been observed in the asymmetric phenylation of cyclic enones with 2-iodo and 2-bromo substituents. The results of this study broaden the scope of the asymmetric additions to ketones promoted by the titanium catalyst derived from ligand 1.

SUBMITTER: Li H 

PROVIDER: S-EPMC397398 | biostudies-literature | 2004 Apr

REPOSITORIES: biostudies-literature

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Catalytic asymmetric addition of diphenylzinc to cyclic alpha,beta-unsaturated ketones.

Li Hongmei H   García Celina C   Walsh Patrick J PJ  

Proceedings of the National Academy of Sciences of the United States of America 20040405 15

We have examined the use of our bis(sulfonamide) diol ligand (1) in the asymmetric addition of phenyl groups to cyclic alpha,beta-unsaturated ketones. Good to excellent enantioselectivities have been obtained with cyclic enones bearing alkyl substituents in the 2 position (71-97% enantiomeric excess). Furthermore, excellent enantioselectivities have been observed in the asymmetric phenylation of cyclic enones with 2-iodo and 2-bromo substituents. The results of this study broaden the scope of th  ...[more]

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