Open AccessStereospecific Construction of Quaternary Carbon Stereocenters from Quaternary Carbon Stereocenters
Author(s) -
Kaushalendra Patel,
Veeranjaneyulu Lanke,
Ilan Marek
Publication year - 2022
Publication title -
journal of the american chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 7.115
H-Index - 612
eISSN - 1520-5126
pISSN - 0002-7863
DOI - 10.1021/jacs.2c01695
Subject(s) - stereocenter , chemistry , stereospecificity , quaternary , nucleophile , stereochemistry , nucleophilic substitution , quaternary carbon , inversion (geology) , enantioselective synthesis , organic chemistry , catalysis , paleontology , geology , structural basin
Organoaluminum species promote a smooth nucleophilic substitution at the quaternary carbon stereocenter of stereodefined polysubstituted cyclopropyl methyl phosphate with a complete inversion of configuration, even when more reactive functional groups are present. The regio- and diastereoselectivity of the substitution is attributed to the existence of a bicyclobutonium intermediate.