Asymmetric Alkylation of Malonic Diester Under Phase-Transfer Conditions

An enantioselective phase-transfer catalytic alkylation of α-monosubstituted malonic diester has been developed. The alkylation of α-monosubstituted tert-butyl methyl malonate in the presence of N-(9-anthracenylmethyl)cinchoninium chloride afforded α,α-disubstituted products in high yields and with...

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Bibliographic Details
Published in:ACS catalysis 2011-10, Vol.1 (10), p.1331-1335
Main Authors: Kanemitsu, Takuya, Koga, Shintaro, Nagano, Daisuke, Miyazaki, Michiko, Nagata, Kazuhiro, Itoh, Takashi
Format: Article
Language:English
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Summary:An enantioselective phase-transfer catalytic alkylation of α-monosubstituted malonic diester has been developed. The alkylation of α-monosubstituted tert-butyl methyl malonate in the presence of N-(9-anthracenylmethyl)cinchoninium chloride afforded α,α-disubstituted products in high yields and with high enantioselectivities. Moreover, a successful gram-scale (10 mmol) experiment using the cinchona catalyst indicates the potential for practical applications of this methodology. To demonstrate the utility of this method, product with a quaternary chiral carbon was converted to both (R)- and (S)-α,α-dialkylated amino acids through alternative chemoselective transformation of the two ester groups.
ISSN:2155-5435
2155-5435
DOI:10.1021/cs200304g