@article{c3f711b7f56b41bb8c656384be5a0f9b,
title = "Palladium(0)-Lithium Iodide Cocatalyzed Asymmetric Hydroalkylation of Conjugated Enynes with Pronucleophiles Leading to 1,3-Disubstituted Allenes",
abstract = "Axially chiral 1,3-disubstituted allenes were synthesized via hydroalkylation of alkyl- or aryl-substituted conjugated enynes (readily prepared via a Sonogashira reaction) with pronucleophiles such as dimethyl malonate under the cocatalysis of DTBM-SEGPHOS-ligated palladium and lithium iodide. Although the palladium catalyst ligated with (S)-DTBM-SEGPHOS prefers the formation of (R)-1,3-disubstituted allenes, lithium iodide recovers and increases the intrinsic selectivity producing (S)-allenes by promoting the isomerization of the exo-alkylidene-π-allylpalladium intermediate prior to the nucleophilic substitution step.",
author = "Hirokazu Tsukamoto and Tatsuya Konno and Kazuya Ito and Takayuki Doi",
note = "Funding Information: This work was partly supported by The Research Foundation for Pharmaceutical Sciences, SUNTRY FOUNDATION for LIFE SCIENCES Platform Project for Supporting Drug Discovery and Life Science Research (Basis for Supporting Innovative Drug Discovery and Life Science Research (BINDS)) from AMED under Grant Number JP18am0101095 and JP18am0101100 and JSPS KAKENHI Grant Numbers JP19K06966 and JP15H05837 in Middle Molecular Strategy. Funding Information: This work was partly supported by The Research Foundation for Pharmaceutical Sciences, SUNTRY FOUNDATION for LIFE SCIENCES, Platform Project for Supporting Drug Discovery and Life Science Research (Basis for Supporting Innovative Drug Discovery and Life Science Research (BINDS)) from AMED under Grant Number JP18am0101095 and JP18am0101100, and JSPS KAKENHI Grant Numbers JP19K06966 and JP15H05837 in Middle Molecular Strategy. Publisher Copyright: Copyright {\textcopyright} 2019 American Chemical Society.",
year = "2019",
month = jul,
day = "14",
doi = "10.1021/acs.orglett.9b02439",
language = "English",
volume = "21",
pages = "6811--6814",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "17",
}