2-pyridylsilyl group as a multifunctional 'phase tag' for solution phase synthesis

Jun ichi Yoshida; Kenichiro Itami; Koichi Mitsudo; Seiji Suga

doi:10.1016/S0040-4039(99)00474-8

2-pyridylsilyl group as a multifunctional 'phase tag' for solution phase synthesis

Jun ichi Yoshida, Kenichiro Itami, Koichi Mitsudo, Seiji Suga

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

49 Citations (Scopus)

Abstract

2-Pyridyldimethylsilyl (2-PyMe₂Si) group was found to serve as effective 'phase tag' for acid-base extraction for solution phase synthesis. Acid-base extraction of octyl(2-pyridyl)dimethylsilane gave rise to 98% recovery. The introduction of 2-PyMe₂Si group to organic molecules was easily accomplished by Rh catalyzed hydrosilylation of alkenes with 2- PyMe₂SiH. The removal of 2-PyMe₂Si group was achieved by the oxidation with H₂O₂/KF (Tamao oxidation). In order to demonstrate the utility of 2- PyMe₂Si group as a 'phase tag', a sequential multi-step transformation was conducted. The products of each steps were easily isolated by acid-base extraction, and were sufficiently pure for the direct use in the next step of the sequence.

Original language	English
Pages (from-to)	3403-3406
Number of pages	4
Journal	Tetrahedron Letters
Volume	40
Issue number	17
DOIs	https://doi.org/10.1016/S0040-4039(99)00474-8
Publication status	Published - Apr 23 1999
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "2-pyridylsilyl group as a multifunctional 'phase tag' for solution phase synthesis",

abstract = "2-Pyridyldimethylsilyl (2-PyMe2Si) group was found to serve as effective 'phase tag' for acid-base extraction for solution phase synthesis. Acid-base extraction of octyl(2-pyridyl)dimethylsilane gave rise to 98% recovery. The introduction of 2-PyMe2Si group to organic molecules was easily accomplished by Rh catalyzed hydrosilylation of alkenes with 2- PyMe2SiH. The removal of 2-PyMe2Si group was achieved by the oxidation with H2O2/KF (Tamao oxidation). In order to demonstrate the utility of 2- PyMe2Si group as a 'phase tag', a sequential multi-step transformation was conducted. The products of each steps were easily isolated by acid-base extraction, and were sufficiently pure for the direct use in the next step of the sequence.",

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

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T1 - 2-pyridylsilyl group as a multifunctional 'phase tag' for solution phase synthesis

AU - Yoshida, Jun ichi

AU - Itami, Kenichiro

AU - Mitsudo, Koichi

AU - Suga, Seiji

PY - 1999/4/23

Y1 - 1999/4/23

N2 - 2-Pyridyldimethylsilyl (2-PyMe2Si) group was found to serve as effective 'phase tag' for acid-base extraction for solution phase synthesis. Acid-base extraction of octyl(2-pyridyl)dimethylsilane gave rise to 98% recovery. The introduction of 2-PyMe2Si group to organic molecules was easily accomplished by Rh catalyzed hydrosilylation of alkenes with 2- PyMe2SiH. The removal of 2-PyMe2Si group was achieved by the oxidation with H2O2/KF (Tamao oxidation). In order to demonstrate the utility of 2- PyMe2Si group as a 'phase tag', a sequential multi-step transformation was conducted. The products of each steps were easily isolated by acid-base extraction, and were sufficiently pure for the direct use in the next step of the sequence.

AB - 2-Pyridyldimethylsilyl (2-PyMe2Si) group was found to serve as effective 'phase tag' for acid-base extraction for solution phase synthesis. Acid-base extraction of octyl(2-pyridyl)dimethylsilane gave rise to 98% recovery. The introduction of 2-PyMe2Si group to organic molecules was easily accomplished by Rh catalyzed hydrosilylation of alkenes with 2- PyMe2SiH. The removal of 2-PyMe2Si group was achieved by the oxidation with H2O2/KF (Tamao oxidation). In order to demonstrate the utility of 2- PyMe2Si group as a 'phase tag', a sequential multi-step transformation was conducted. The products of each steps were easily isolated by acid-base extraction, and were sufficiently pure for the direct use in the next step of the sequence.

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 17

ER -

2-pyridylsilyl group as a multifunctional 'phase tag' for solution phase synthesis

Abstract

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