Enantioselective Intramolecular CH-Insertions upon Cu-Catalyzed Decomposition of Phenyliodonium Ylides

doi:10.3390/60300258

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Molecules 2001, 6(3), 258-266; doi:10.3390/60300258

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Enantioselective Intramolecular CH-Insertions upon Cu-Catalyzed Decomposition of Phenyliodonium Ylides

Paul Müller* and Christelle Boléa

Department of Organic Chemistry, University of Geneva 30, Quai Ernest-Ansermet, CH-1211 Geneva 4, Switzerland

* Author to whom correspondence should be addressed.

Received: 24 January 2001 / Accepted: 7 February 2001 / Published: 28 February 2001

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Abstract: The Cu-catalyzed intramolecular CH insertion of phenyliodonium ylide 5b has been investigated at 0° C in the presence of several chiral ligands. Enantioselectivities vary in the range of 38–72 %, and are higher than those resulting from reaction of the diazo compound 5c at 65° C. The results are consistent with a carbenoid mechanism for Cu-catalyzed decomposition of phenyliodonium ylides.

Keywords: Phenyliodonium ylides; CH insertion; Cu-catalysis; asymmetric induction

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MDPI and ACS Style

Müller, P.; Boléa, C. Enantioselective Intramolecular CH-Insertions upon Cu-Catalyzed Decomposition of Phenyliodonium Ylides. Molecules 2001, 6, 258-266.

AMA Style

Müller P., Boléa C. Enantioselective Intramolecular CH-Insertions upon Cu-Catalyzed Decomposition of Phenyliodonium Ylides. Molecules. 2001; 6(3):258-266.

Chicago/Turabian Style

Müller, Paul; Boléa, Christelle. 2001. "Enantioselective Intramolecular CH-Insertions upon Cu-Catalyzed Decomposition of Phenyliodonium Ylides." Molecules 6, no. 3: 258-266.

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