Transformation of aldehydes into (E)-1-alkenylsilanes and (E)-1-alkenylboronic esters with a catalytic amount of a chromium salt

Kazuhiko Takai; Yuji Kunisada; Yukiko Tachibana; Nana Yamaji; Emi Nakatani

doi:10.1246/bcsj.77.1581

Transformation of aldehydes into (E)-1-alkenylsilanes and (E)-1-alkenylboronic esters with a catalytic amount of a chromium salt

Kazuhiko Takai, Yuji Kunisada, Yukiko Tachibana, Nana Yamaji, Emi Nakatani

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18 Citations (Scopus)

Abstract

(Diiodomethyl)trimethylsilane (Me₃SiCHI₂, 1) is produced by treatment of iodoform with manganese in the presence of Me ₃SiCl. Aldehydes are converted to (E)-1-trimethylsilyl-1-alkenes in a stereoselective manner with a geminal dichromium reagent generated from 1, manganese, Me₃SiCl, and a catalytic amount of CrCl ₃[thf]₃ in THF. Similarly, (E)-1-alkenylboronic esters are prepared stereoselectively in good to excellent yields by treatment of aldehydes with a geminal dichromium reagent derived from Cl₂CHB(OR) ₂ [(OR)₂ = OCMe₂CMe₂O] and LiI instead of 1.

Original language	English
Pages (from-to)	1581-1586
Number of pages	6
Journal	Bulletin of the Chemical Society of Japan
Volume	77
Issue number	8
DOIs	https://doi.org/10.1246/bcsj.77.1581
Publication status	Published - Aug 2004

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Cite this

Takai, K., Kunisada, Y., Tachibana, Y., Yamaji, N., & Nakatani, E. (2004). Transformation of aldehydes into (E)-1-alkenylsilanes and (E)-1-alkenylboronic esters with a catalytic amount of a chromium salt. Bulletin of the Chemical Society of Japan, 77(8), 1581-1586. https://doi.org/10.1246/bcsj.77.1581

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title = "Transformation of aldehydes into (E)-1-alkenylsilanes and (E)-1-alkenylboronic esters with a catalytic amount of a chromium salt",

abstract = "(Diiodomethyl)trimethylsilane (Me3SiCHI2, 1) is produced by treatment of iodoform with manganese in the presence of Me 3SiCl. Aldehydes are converted to (E)-1-trimethylsilyl-1-alkenes in a stereoselective manner with a geminal dichromium reagent generated from 1, manganese, Me3SiCl, and a catalytic amount of CrCl 3[thf]3 in THF. Similarly, (E)-1-alkenylboronic esters are prepared stereoselectively in good to excellent yields by treatment of aldehydes with a geminal dichromium reagent derived from Cl2CHB(OR) 2 [(OR)2 = OCMe2CMe2O] and LiI instead of 1.",

author = "Kazuhiko Takai and Yuji Kunisada and Yukiko Tachibana and Nana Yamaji and Emi Nakatani",

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T1 - Transformation of aldehydes into (E)-1-alkenylsilanes and (E)-1-alkenylboronic esters with a catalytic amount of a chromium salt

AU - Takai, Kazuhiko

AU - Kunisada, Yuji

AU - Tachibana, Yukiko

AU - Yamaji, Nana

AU - Nakatani, Emi

PY - 2004/8

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N2 - (Diiodomethyl)trimethylsilane (Me3SiCHI2, 1) is produced by treatment of iodoform with manganese in the presence of Me 3SiCl. Aldehydes are converted to (E)-1-trimethylsilyl-1-alkenes in a stereoselective manner with a geminal dichromium reagent generated from 1, manganese, Me3SiCl, and a catalytic amount of CrCl 3[thf]3 in THF. Similarly, (E)-1-alkenylboronic esters are prepared stereoselectively in good to excellent yields by treatment of aldehydes with a geminal dichromium reagent derived from Cl2CHB(OR) 2 [(OR)2 = OCMe2CMe2O] and LiI instead of 1.

AB - (Diiodomethyl)trimethylsilane (Me3SiCHI2, 1) is produced by treatment of iodoform with manganese in the presence of Me 3SiCl. Aldehydes are converted to (E)-1-trimethylsilyl-1-alkenes in a stereoselective manner with a geminal dichromium reagent generated from 1, manganese, Me3SiCl, and a catalytic amount of CrCl 3[thf]3 in THF. Similarly, (E)-1-alkenylboronic esters are prepared stereoselectively in good to excellent yields by treatment of aldehydes with a geminal dichromium reagent derived from Cl2CHB(OR) 2 [(OR)2 = OCMe2CMe2O] and LiI instead of 1.

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10.1246/bcsj.77.1581