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Diastereoselectivity in the Addition of Allylzinc Reagents to δ ‐Alkoxy‐ γ , δ ‐disubstituted Alkenyllithium Compounds
Author(s) -
Bernard Nicolas,
Chemla Fabrice,
Ferreira Franck,
Mostefai Naouel,
Normant JeanF.
Publication year - 2002
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/1521-3765(20020715)8:14<3139::aid-chem3139>3.0.co;2-7
Subject(s) - alkoxy group , reagent , chemistry , conformational isomerism , bromide , oxygen atom , allyl bromide , chelation , medicinal chemistry , combinatorial chemistry , stereochemistry , organic chemistry , alkyl , molecule
The carbometalation reaction of allyl‐ and crotylzinc bromide with metalated disubstituted homoallylic ethers gives tri‐ or tetrasubstituted 5‐hexenyl ethers with excellent control of the diastereoselectivity. The stereochemistry of this reaction is discussed and has been attributed to an early transition state with chelation to the oxygen atom in the energetically favored conformer as the stereodetermining step.