Open AccessPreparation of Enantioenriched Alkylcarbastannatranes via Nucleophilic Inversion of Alkyl Mesylates for Use in Stereospecific Cross-Coupling Reactions
Author(s) -
Glenn Ralph,
Mark R. Biscoe
Publication year - 2019
Publication title -
organometallics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.231
H-Index - 172
eISSN - 1520-6041
pISSN - 0276-7333
DOI - 10.1021/acs.organomet.9b00467
Subject(s) - stereospecificity , chemistry , sn2 reaction , alkyl , nucleophile , inversion (geology) , nucleophilic substitution , coupling reaction , combinatorial chemistry , optically active , medicinal chemistry , stereochemistry , organic chemistry , catalysis , paleontology , structural basin , biology
We report the preparation of enantioenriched secondary alkylcarbastannatranes via a stereoinvertive S N 2 reaction of enantioenriched alkyl mesylates and carbastannatranyl anion equivalents. Using this process, enantioenriched secondary alcohols may be converted into highly enantioenriched alkylcarbastannatranes, which are useful in stereospecific cross-coupling reactions.