ChemInform Abstract: SN2′ Additions of Cuprates to Sulfone and Ester-Polarized Cyclopentenylic Systems.
Abstract
The stereochemistry of SN2' addition of cuprate to sulfones and ester-polarized cyclopentenyl systems is shown to often depend upon the nature of the leaving group.
ChemInform Abstract
The stereochemistry of SN2' addition of cuprate to sulfones and ester-polarized cyclopentenyl systems is shown to often depend upon the nature of the leaving group. However, the cis-disubstituted substrates (I), (IV), (V) and (VII) all react with dimethylcuprate (generated from MeLi + CuI) via the anti SN2' transition state to give the products (III) and (VI). By contrast, the trans-disubstituted cyclopentene derivatives (VIII) undergo a rapid synfacial SN2' reaction (usually typical for allyl ammonium salts) to produce the adducts (IX), whereas the anti SN2' product (XI) is obtained from the sulfonium salt (X).
