A Novel Class of Tunable Zinc Reagents (RXZnCH2Y) for Efficient Cyclopropanation of Olefins
- 17 December 2003
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 69 (2), 327-334
- https://doi.org/10.1021/jo030312v
Abstract
A class of zinc reagents (RXZnCH(2)Y) generated with an appropriate organozinc is very effective for the cyclopropanation of olefins. The reactivity and selectivity of these reagents can be regulated by tuning the electronic and steric nature of the RX group on Zn. A reasonable level of enantioselectivity was obtained for the cyclopropanation of unfunctionalized olefins when a chiral (iodomethyl)zinc species was used, providing a valuable approach for the asymmetric cyclopropanation of unfunctionalized olefins.Keywords
This publication has 56 references indexed in Scilit:
- The Stereochemistry of Carbenoid Cyclopropanation ReactionsChemistry – A European Journal, 1995
- Photochemistry of phenyl-substituted benzobicyclo[3.1.0]hex-2-enes. A reverse di-.pi.-methane rearrangementThe Journal of Organic Chemistry, 1983
- Nucleophilic step of the ring opening reactions of cyclopropanes with electrophiles. Mechanism and stereochemistry. I. Reaction of 1-phenylbicyclo[4.1.0]heptane with mercuric saltsThe Journal of Organic Chemistry, 1975
- Synthesis via silyl alkenyl ethers. IV. Synthesis of 1-hydroxybicyclo[n.1.0]alkanes from silyl alkenyl ethers. Novel class of cyclopropanolsThe Journal of Organic Chemistry, 1973
- Reaction of trimethysilyl enol ethers with Simmons-Smith reagent. Facile synthesis of trimethylsilyl cyclopropyl ethers and cyclopropanolsThe Journal of Organic Chemistry, 1973
- Reductive conversion of 1-aryl-3-hydroxymethyl-3,4-dihydro-2-naphthoic acid lactones into substituted tetrahydro-1H-cyclopropa[a]naphthalenesThe Journal of Organic Chemistry, 1972
- Cyclopropyl aromatic chemistry. I. Ultraviolet spectra of certain cyclopropyl aromatic systemsJournal of the American Chemical Society, 1969
- Cyclopropane Synthesis from Methylene Iodide, Zinc-Copper Couple, and Olefins. II.1 Nature of the IntermediateJournal of the American Chemical Society, 1964
- A New Synthesis of Cyclopropanes1Journal of the American Chemical Society, 1959
- A NEW SYNTHESIS OF CYCLOPROPANES FROM OLEFINSJournal of the American Chemical Society, 1958