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Synlett 2001; 2001(12): 1851-1854
DOI: 10.1055/s-2001-18761
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A High Yield Procedure for the Me3SiNTf2-Induced Carbon-Carbon Bond-Forming Reactions of Silyl Nucleophiles with Carbonyl Compounds: The Importance of Addition Order and Solvent Effects

Kazuaki Ishihara* , Yukihiro Hiraiwa, Hisashi Yamamoto
  • *Graduate School of Engineering, Nagoya University, CREST, Japan Science of Technology Corporation (JST), Furo-cho, Chikusa, Nagoya 464-8603, Japan; Fax: + 81(52)7893222; E-mail: yamamoto@cc.nagoya-u.ac.jp
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Publication Date:
04 December 2001 (online)

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We demonstrate the efficiency of Me3SiNTf2 (0.3-1.0 mol%) as a strong Lewis acid catalyst for the Mukaiyama aldol and Sakurai-Hosomi allylation reactions, and that the slow addition of carbonyl compounds to a solution of acid catalyst and Me3Si-Nu is very important for suppressing side products; this may be widely accepted as a common and reasonable general procedure for the Lewis acid-induced reaction of Me3Si-Nu with carbonyl compounds.

Lewis acid - catalyst - Mukaiyama aldol reaction - Sakurai-Hosomi allylation reaction - green chemistry

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