Phase Transfer Catalyst (PTC) Catalyzed Alkylations of Glycinamides for Asymmetric Syntheses of $\alpha$-Amino Acid Derivatives

The chiral amine auxiliary mediated stereoselective alkylation reactions of glycinamides 1-6 and 15-17 using phase transfer catalyst (PTC) for liquid-solid extraction are described. The secondary N-(diphenylmethylene) glycinamides 1, 2 and 3 give better selectivities and yields than tertiary N-(diph...

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Bibliographic Details
Published in:Bulletin of the Korean Chemical Society 2001, Vol.22 (9), p.958-962
Main Authors: 박선영, 김현주, 임동열, Park, Seon Yeong, Kim, Hyeon Ju, Im, Dong Yeol
Format: Article
Language:Korean
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Summary:The chiral amine auxiliary mediated stereoselective alkylation reactions of glycinamides 1-6 and 15-17 using phase transfer catalyst (PTC) for liquid-solid extraction are described. The secondary N-(diphenylmethylene) glycinamides 1, 2 and 3 give better selectivities and yields than tertiary N-(diphenylmethylene) glycinamides 4, 5 and 6. Alkylation of the glycinamide 1 and 2 using 18-Crown-6 as a PTC in toluene at $-40^{\circ}C$ gives best selectivities and yields. Alkylations of N-(4-chlorophenylmethylene)glycinamides 15, 16 and 17 under same PTC conditions give $\alpha$, $\alpha-disubstituted$ amino acid derivatives 18, 19 and 20 with low diastereoselectivities.
ISSN:0253-2964
1229-5949