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Diastereoselective Coupling of Chiral Acetonide Trisubstituted Radicals with Alkenes
Author(s) -
Tao Daniel J.,
Muuronen Mikko,
Slutskyy Yuriy,
Le Alexander,
Furche Filipp,
Overman Larry E.
Publication year - 2016
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/chem.201601957
Subject(s) - radical , chemistry , acetonide , nucleophile , hydrogen bond , coupling (piping) , photochemistry , medicinal chemistry , stereochemistry , organic chemistry , catalysis , molecule , materials science , metallurgy , medicine , surgery , triamcinolone acetonide
The stereochemical outcome of reactions of chiral nucleophilic trisubstituted acetonide radicals with electron‐deficient alkenes is dictated by a delicate balance between destabilizing non‐bonding interactions and stabilizing hydrogen‐bonding between substituents on the α and β carbons.