Concepedia

Optimization of enantiocontrol in cis-selective cyclopropanation reactions catalyzed by dirhodium(ii) tetrakis[alkyl 2-oxaazetidine-4(S)-carboxylates]

Michael P. Doyle, Simon B. Davies, Wenhao Hu

Chemical Communications · 2000 · 44 citations · 7 references

DOI

Concepts

Abstract

Both intermolecular and macrocyclic intramolecular cyclopropanation reactions occur with greater selectivity for the cis-(Z)-diastereoisomer than for the trans-(E)-diastereomer in reactions catalyzed by chiral dirhodium(II) azetidinone-carboxylates; the influence of the catalyst’s ester alkyl group on enantiocontrol is substantial but appears to be delicately balanced by steric factors.

References

7

New aspects of catalytic asymmetric cyclopropanation

Michael P. Doyle, Marina Protopopova · Tetrahedron · 1998 · 313 citations

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Asymmetric copper-catalyzed cyclopropanation of trisubstituted and unsymmetrical cis-1,2-disubstituted olefins: modified bis-oxazoline ligands

Richard Lowenthal, Satoru Masamune · Tetrahedron Letters · 1991 · 299 citations

, , +10

Asymmetric synthesis of lactones with high enantioselectivity by intramolecular carbon-hydrogen insertion reactions of alkyl diazoacetates catalyzed by chiral rhodium(II) carboxamides

Michael P. Doyle, Arjan van Oeveren, Larry J. Westrum et al. · Journal of the American Chemical Society · 1991 · 143 citations

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Enantioselective metal carbene transformations with polyethylene-bound soluble recoverable dirhodium(II) 2-pyrrolidone-5(S)-carboxylates

Michael P. Doyle, Michail Y. Eismont, David E. Bergbreiter et al. · The Journal of Organic Chemistry · 1992 · 90 citations

, , +5

Formation of Macrocyclic Lactones by Enantioselective Intramolecular Cyclopropanation of Diazoacetates Catalyzed by Chiral Cu<sup><scp>I</scp></sup> and Rh<sup><scp>II</scp></sup> Compounds

Michael P. Doyle, Chad S. Peterson, Dann L. Parker · Angewandte Chemie International Edition in English · 1996 · 87 citations

, , +10