Enantioselective tandem formation and [2,3]-sigmatropic rearrangement of cyclic propargylic oxonium ylides catalyzed by dirhodium(II) tetrakis[N-phthaloyl-(S)-tert-leucinate]

被引：18
|
作者：
Tsutsui, H [1 ]
Matsuura, M [1 ]
Makino, K [1 ]
Nakamura, S [1 ]
Nakajima, M [1 ]
Kitagaki, S [1 ]
Hashimoto, S [1 ]
机构：
[1] Hokkaido Univ, Grad Sch Pharmaceut Sci, Sapporo, Hokkaido 0600812, Japan
来源：
ISRAEL JOURNAL OF CHEMISTRY | 2001年 / 41卷 / 04期
关键词：
D O I：
10.1092/E7M9-EM8U-TP1B-41HB
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
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 (alpha-diazo-beta-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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页码：283 / 295
页数：13
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