Asymmetric Alkylation of Malonic Diester Under Phase-Transfer Conditions

作者：Kanemitsu Takuya; Koga Shintaro; Nagano Daisuke; Miyazaki Michiko; Nagata Kazuhiro; Itoh Takashi^*

来源：ACS Catalysis, 2011, 1(10): 1331-1335.

DOI：10.1021/cs200304g

• organocatalysis
• asymmetric synthesis
• phase-transfer catalysis
• quaternary stereocenter
• malonic ester

An enantioselective phase-transfer catalytic alkylation of alpha-monosubstituted malonic diester has been developed. The alkylation of alpha-monosubstituted tert-butyl methyl malonate in the presence of N-(9-anthracenylmethyl)cinchoninium chloride afforded alpha,alpha-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)-alpha, alpha-dialkylated amino acids through alternative chemoselective transformation of the two ester groups.

• 出版日期2011-10