Synthesis 2003(14): 2189-2193
DOI: 10.1055/s-2003-41017
PAPER
© Georg Thieme Verlag Stuttgart · New York

Efficient Addition of Allylsilanes to α,β-Enones Using Catalytic Indium and Trimethylsilyl Chloride

Phil Ho Lee*, Dong Seomoon, Sundae Kim, K. Nagaiah, S. V. Damle, Kooyeon Lee
Department of Chemistry, Kangwon National University, Chunchon 200-701, Republic of Korea
Fax: +82(33)2537582; e-Mail: phlee@kangwon.ac.kr;
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Publikationsverlauf

Received 3 June 2003
Publikationsdatum:
19. August 2003 (online)

Abstract

α,β-Enones undergo an efficient Hosomi-Sakurai reaction with allyltrimethylsilane, in which a catalytic amount of indium is used in the presence of trimethylsilyl chloride as an activator under mild conditions to produce the conjugate addition products in good yields.

10

14a was prepared from 1,3-cyclohexadione in 5 steps (PhH, EtOH, TsOH; LDA, allyl iodide; DIBALH; H3O+; Wacker oxidation).

12

Compound 15a was prepared from 1,3-cyclohexadione in 7 steps (PhH, EtOH, TsOH; LDA, allyl iodide; Sia2BH, H2O2, NaOH; Swern oxidation; Ph3P=CHCH2TMS; DIBALH; H3O+).