(2-Pyridyldimethylsilyl)methyl lithium as a novel hydroxymethylating reagent

Kenichiro Itami; Koichi Mitsudo; Jun ichi Yoshida

doi:10.1016/S0040-4039(99)01028-X

(2-Pyridyldimethylsilyl)methyl lithium as a novel hydroxymethylating reagent

Kenichiro Itami, Koichi Mitsudo, Jun ichi Yoshida

Research output: Contribution to journal › Article › peer-review

31 Citations (Scopus)

Abstract

(2-Pyridyldimethylsilyl)methyl lithium was found to react with organic bromides, aldehydes, ketones, and hydrosilanes in good to excellent yields. The resultant adducts were further oxidized with H₂O₂/KF to give the corresponding alcohols in excellent yields. Thus, this two-step transformation provides an efficient method for hydroxymethylation.

Original language	English
Pages (from-to)	5537-5540
Number of pages	4
Journal	Tetrahedron Letters
Volume	40
Issue number	30
DOIs	https://doi.org/10.1016/S0040-4039(99)01028-X
Publication status	Published - Jul 1 1999
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "(2-Pyridyldimethylsilyl)methyl lithium as a novel hydroxymethylating reagent",

abstract = "(2-Pyridyldimethylsilyl)methyl lithium was found to react with organic bromides, aldehydes, ketones, and hydrosilanes in good to excellent yields. The resultant adducts were further oxidized with H2O2/KF to give the corresponding alcohols in excellent yields. Thus, this two-step transformation provides an efficient method for hydroxymethylation.",

author = "Kenichiro Itami and Koichi Mitsudo and Yoshida, {Jun ichi}",

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AU - Itami, Kenichiro

AU - Mitsudo, Koichi

AU - Yoshida, Jun ichi

PY - 1999/7/1

Y1 - 1999/7/1

N2 - (2-Pyridyldimethylsilyl)methyl lithium was found to react with organic bromides, aldehydes, ketones, and hydrosilanes in good to excellent yields. The resultant adducts were further oxidized with H2O2/KF to give the corresponding alcohols in excellent yields. Thus, this two-step transformation provides an efficient method for hydroxymethylation.

AB - (2-Pyridyldimethylsilyl)methyl lithium was found to react with organic bromides, aldehydes, ketones, and hydrosilanes in good to excellent yields. The resultant adducts were further oxidized with H2O2/KF to give the corresponding alcohols in excellent yields. Thus, this two-step transformation provides an efficient method for hydroxymethylation.

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