N-Sulfinyl Metalloenamine Conjugate Additions: Asymmetric Synthesis of Piperidines
The Journal of Organic Chemistry2005Vol. 70(18), pp. 7342–7345
Citations Over TimeTop 14% of 2005 papers
Abstract
[reaction: see text] The first examples of conjugate additions of N-tert-butanesulfinyl metalloenamines are reported. Highly stereoselective conjugate additions (97:3 to 99:1 dr) were observed between metalloenamines derived from N-sulfinyl ketimines and alpha,beta-unsaturated ketones bearing either alkyl or aryl substituents. The conjugate addition products could rapidly be converted with high diastereoselectivity to 2,4,6-trisubstituted piperidines, which are difficult to access by other methods.
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