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Enantioselective Protonation of Radical Anion Intermediates in Photoallylation and Photoreduction Reactions of 3,3-Diaryl-1,1-dicyano-2-methylprop-1-ene With Allyltrimethylsilane

Enantioselective Protonation of Radical Anion Intermediates in Photoallylation and Photoreduction Reactions of 3,3-Diaryl-1,1-dicyano-2-methylprop-1-ene With Allyltrimethylsilane

Hajime Maeda, Masayuki Iida, Daisuke Ogawa, Kazuhiko Mizuno

Molecules. 2019 Jul 23;24(14):2677.

PMID: 31340614

Abstract:

Photoreactions of acetonitrile solutions of 3,3-diaryl-1,1-dicyano-2-methylprop-1-enes (1a-c) with allyltrimethylsilane (2) in the presence of phenanthrene as a photoredox catalyst and acetic acid as a proton source formed photoallylation (3) and photoreduction (4) products via photoinduced electron transfer pathways. When (S)-mandelic acid was used as the proton source, the reactions proceeded with 3.4 and 4.8 %ee for formation of 3 and 4, respectively. The results of studies of the effect of aryl ring substituents and several chiral carboxylic acids suggested that the enantioselectivities of the reactions are governed by steric controlled proton transfer in intermediate complexes formed by π-π and OH-π interactions of anion radicals derived from 1a-c and chiral carboxylic acids.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP762721	Allyltrimethylsilane		762-72-1	Price

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