Palladium(0)–Lithium Iodide Cocatalyzed Asymmetric
Hydroalkylation of Conjugated Enynes with Pronucleophiles Leading
to 1,3-Disubstituted Allenes
Version 4 2019-08-26, 15:42
Version 3 2019-08-26, 15:38
Version 2 2019-08-23, 17:42
Version 1 2019-08-23, 17:39
Posted on 2019-08-26 - 15:42
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.
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Tsukamoto, Hirokazu; Konno, Tatsuya; Ito, Kazuya; Doi, Takayuki (2019). Palladium(0)–Lithium Iodide Cocatalyzed Asymmetric
Hydroalkylation of Conjugated Enynes with Pronucleophiles Leading
to 1,3-Disubstituted Allenes. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.9b02439
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