2-Pyridylsilyl group as a multifunctional “phase tag" for solution phase synthesis
1999; Elsevier BV; Volume: 40; Issue: 17 Linguagem: Inglês
10.1016/s0040-4039(99)00474-8
ISSN1873-3581
AutoresJun‐ichi Yoshida, Kenichiro Itami, Koichi Mitsudo, Seiji Suga,
Tópico(s)Asymmetric Synthesis and Catalysis
Resumo2-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 withH/2O2KF(Tamao oxidation). In order to demonstrate the utilitiy 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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