Iodomethylzinc Phosphates: Powerful Reagents for the Cyclopropanation of Alkenes
- 19 August 2005
- journal article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 127 (36), 12440-12441
- https://doi.org/10.1021/ja0529687
Abstract
A new family of zinc carbenoids derived from phosphoric acids was developed and used in the cyclopropanation of allylic alcohols and ethers and also of unfunctionalized olefins. The use of the chiral phosphoric acid of a 3,3‘-disubstituted BINOL leads to efficient stereocontrol, affording the cyclopropanes of allylic and homoallylic ethers with complete conversions and up to 93% ee. A catalytic version of this reaction using 10 mol % of the chiral phosphate reagent is also disclosed.Keywords
This publication has 6 references indexed in Scilit:
- Stereoselective Cyclopropanation ReactionsChemical Reviews, 2003
- New Family of Cyclopropanating Reagents: Synthesis, Reactivity, and Stability Studies of Iodomethylzinc PhenoxidesAngewandte Chemie-International Edition, 2000
- Preparation, Solid-State Structure, and Synthetic Applications of Isolable and Storable Haloalkylzinc ReagentsJournal of the American Chemical Society, 2000
- One-flask, regiospecific conversions of allylic alcohols into 2-carbon-extended, conjugated dienoate esters. Use of a new sulfinyl orthoesterThe Journal of Organic Chemistry, 1991
- Synthesis of cyclopropanes by the reaction of olefins with dialkylzinc and methylene iodideTetrahedron, 1968
- A NEW SYNTHESIS OF CYCLOPROPANES FROM OLEFINSJournal of the American Chemical Society, 1958