Double Asymmetric Induction in Intramolecular C-H Insertion Reactions ofα-Diazoβ-Keto Esters
- 1 December 1994
- journal article
- research article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 24 (22), 3277-3287
- https://doi.org/10.1080/00397919408010251
Abstract
A new double asymmetric induction in C-C bond formation has been achieved by the use of dirhodium(II) tetrakis[N-phthaloyl-(R) or (S)-phenylalaninate] as a homochiral catalyst in intramolecular C-H insertion of α-diazo β-keto esters of homochiral alcohols. The matched combination of the (+)-neomenthyl esters and the catalyst derived from (R)-phenylalanine produces, after a removal of the ester group, optically active 3-substituted cyclopentanones of up to 80% ee.Keywords
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