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

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‐...

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Bibliographic Details
Published in:Israel journal of chemistry 2001-12, Vol.41 (4), p.283-296
Main Authors: Tsutsui, Hideyuki, Matsuura, Maya, Makino, Kazuishi, Nakamura, Seiichi, Nakajima, Makoto, Kitagaki, Shinji, Hashimoto, Shunichi
Format: Article
Language:English
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Summary: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.
ISSN:0021-2148
1869-5868
DOI:10.1560/E7M9-EM8U-TP1B-41HB