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Type: Artigo de periódico
Title: The addition of allyltrimethylsilane to cyclic N-acyliminium ions derived from (S)-(+)-mandelic acid and cyclohexyl-based chiral auxiliaries
Author: D'Oca, MGM
Pilli, RA
Pardini, VL
Curi, D
Comninos, FCM
Abstract: The TiCl4- promoted addition of allyltrimethylsilane to chiral 5- and 6-membered N-acyliminium ions employing (S)-(+)-mandelic acid, (1R, 2S)-trans-2-phenyl-1-cyclohexanol and (1R,2S,5R)-8-phenylmenthol derivatives as chiral auxiliaries occurred with low to moderate diastereoisomeric ratios (1:1-6:1) to afford 2-substituted amides and carbamates in good yields. The best diastereoselection was observed with (1R,2S,5R)-8-phenylmenthol as the chiral auxiliary. The 2-substituted amides and carbamates were converted to the corresponding alkaloids (S)- and (R)-propyl pyrrolidine and coniine with efficient recovery of the chiral auxiliaries.
Subject: (S)-(+)-mandelic acid
cyclohexyl-based chiral auxiliaries
N-acyliminium ions
pyrrolidine and piperidine derivatives
Country: Brasil
Editor: Soc Brasileira Quimica
Citation: Journal Of The Brazilian Chemical Society. Soc Brasileira Quimica, v. 12, n. 4, n. 507, n. 513, 2001.
Rights: aberto
Date Issue: 2001
Appears in Collections:Unicamp - Artigos e Outros Documentos

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