Enantioselective tandem formation and [2,3]‐sigmatropic rearrangement of cyclic propargylic oxonium ylides catalyzed by dirhodium(II) tetrakis[N‐phthaloyl‐(S)‐tert‐leucinate]
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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四[N-邻苯二甲酰-(S)-叔亮氨酸]二铑(II)催化环状炔丙基氧鎓叶立德的对映选择性串联形成和[2,3]-σ重排
DOI：
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发表时间：
2001
期刊：
影响因子：
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通讯作者：
S. Hashimoto*
中科院分区：
文献类型：
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作者：
H. Tsutsui;M. Matsuura;K. Makino;Seiichi Nakamura;M. Nakajima;S. Kitagaki;S. Hashimoto*
本文首次报道了重氮催化分解生成的炔丙基氧鎓叶立德的近选择性[2，3]-σ迁移重排反应中催化剂依赖的不对称诱导。在甲苯中使用四[N-邻苯二甲酰基-（S）-叔-亮氨酸]二铑（II）对α-重氮-s-酮酯4a-g进行催化，导致几乎完全形成带有丙二烯基的苯并呋喃-3-酮，其ee高达79%。
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-s-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.