ChemInform Abstract: Stereoselective Radical Carbon-Carbon Bond Forming Reactions of β- Alkoxy Esters: Atom and Group Transfer Allylations under Bidentate Chelation Controlled Conditions.
✍ Scribed by Y. GUINDON; B. GUERIN; C. CHABOT; W. OGILVIE
- Publisher
- John Wiley and Sons
- Year
- 2010
- Weight
- 36 KB
- Volume
- 28
- Category
- Article
- ISSN
- 0931-7597
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✦ Synopsis
Stereoselective Radical Carbon-Carbon Bond Forming Reactions of β-Alkoxy Esters: Atom and Group Transfer Allylations under Bidentate Chelation Controlled Conditions.
-The allylation of several β-alkoxy esters such as (I) in the presence of MgBr2•OEt2 occurs under bidentate chelation-controlled conditions to afford selectively the anti-products (III). The reactions work with iodides and bromides as well as phenylselenides. However, in contrast with the anti iodide (Ia) the corresponding syn iodide undergoes no allylation. This effect is only minor in the case of bromides and absent in the case of phenylselenides. The results are discussed in terms of a radical atom transfer mechanism and represent the first example of an atom transfer reaction in which facial selectivity is controlled by Lewis acid complexation. -(GUINDON, Y.;