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Chirality Transfer from Carbon to Nitrogen to Carbon via Cyclic Ammonium Ylides

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journal contribution
posted on 17.05.1999 by Kevin W. Glaeske, F. G. West
Cyclic ammonium salts 2 were prepared by diastereoselective quaternization of nitrogen in the corresponding proline or threonine derivatives. Upon treatment with base, salts 2 underwent [1,2]- or [2,3]-shift to 3 with moderate to complete stereospecificity. The overall process entails chirality transfer from the original α carbon to the neighboring nitrogen and then back to the carbon.

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