Enantioselective tandem formation and [2,3]-sigmatropic rearrangement of cyclic propargylic oxonium ylides catalyzed by dirhodium(II) tetrakis[N-phthaloyl-(S)-tert-leucinate] |
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Authors: | Hideyuki Tsutsui Maya Matsuura Kazuishi Makino Seiichi Nakamura Makoto Nakajima Shinji Kitagaki Shunichi Hashimoto |
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Affiliation: | Graduate School of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan |
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Abstract: | This paper describes the first examples of catalyst-dependent asymmetric induction in the periselective [2,3]-sigmatropic rearrangement of propargylic oxonium ylides generated by catalytic diazo decomposition. Catalysis of α-diazo-ß-keto esters 4a—g using dirhodium(II) tetrakis[N-phthaloyl-(S)-tert-leucinate] in toluene has led to the virtually exclusive formation of benzofuran-3-ones bearing an allenic group with up to 79% ee. |
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