Selectivity Enhancement in the Rh(II)-Catalyzed Cyclopropanation of Styrene with (Silanyloxyvinyl)diazoacetates
- 23 April 2004
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 6 (11), 1725-1728
- https://doi.org/10.1021/ol049554n
Abstract
The cyclopropanation of styrene with (silanyloxyvinyl)diazoacetates proceeds with exceptional diastereo- and enantioselectivity in the presence of chiral Rh(II) catalysts. 1,8-Naphthoyl-protected amino acids are the most effective Rh(II) ligands for these transformations.Keywords
This publication has 10 references indexed in Scilit:
- Rhodium(II)-catalyzed enantioselective intramolecular CH insertion with alkyl diazo(trialkylsilyl) acetatesTetrahedron: Asymmetry, 2003
- Rhodium(II)-catalyzed olefin cyclopropanation with the phenyliodonium ylide derived from Meldrum's acidTetrahedron: Asymmetry, 2003
- RhII-catalyzed cycloadditions of carbomethoxy iodonium ylidesTetrahedron Letters, 2002
- Catalytic enantioselective rearrangements and cycloadditions involving ylides from diazo compoundsChemical Society Reviews, 2000
- An efficient route to chiral, non-racemic 3-alkyl-3-arylpyrrolidines. Improved stereoselectivity in alkylation of bicyclic lactams and the effect of leaving groupsTetrahedron Letters, 2000
- Absolute structure and absolute configurationActa Crystallographica Section A Foundations of Crystallography, 1999
- Effect of diazoalkane structure on the stereoselectivity of rhodium(II) (S)-N-(arylsulfonyl)prolinate catalyzed cyclopropanationsTetrahedron Letters, 1996
- Heteroaromatic N-oxide rearrangements. Reinvestigation of 1,3 tosyloxy migration in the reaction of isoquinoline N-oxide with tosyl chlorideTetrahedron Letters, 1993
- Electrophilic metal carbenes as reaction intermediates in catalytic reactionsAccounts of Chemical Research, 1986
- Occurrence of the SN(ANRORC) mechanism in the hydrazination of 1,2,4,5-tetrazinesThe Journal of Organic Chemistry, 1981