Stereocontrolled (Me3Si)3SiH-Mediated Radical and Ionic Hydride Transfer in Synthesis of 2,3,5-Trisubstituted THF | Zendy

Simon Grélaud | Zendy; Valérie Desvergnes | Zendy; Yannick Landais | Zendy

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Stereocontrolled (Me₃Si)₃SiH-Mediated Radical and Ionic Hydride Transfer in Synthesis of 2,3,5-Trisubstituted THF

Author(s) -

Simon Grélaud,

Valérie Desvergnes,

Yannick Landais

Publication year - 2016

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.6b00303

Subject(s) - chemistry , hydride , ionic bonding , medicinal chemistry , ion , organic chemistry , hydrogen

2,3,5-Trisubstituted tetrahydrofurans were prepared stereoselectively through a two-step process involving the addition of an acyl radical to a β-silyloxy acrylic ester followed by an acid-catalyzed desilylation-ketalization sequence and a final oxocarbenium reduction step. High levels of 1,2- and 1,3-stereocontrol were attained when (Me3Si)3SiH was used as a radical followed by a ionic hydrogen transfer agent.

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