Enantioselective synthesis of α-halo-α-alkylmalonates via phase-transfer catalytic α-alkylation

Hong, Suckchang; Kim, Minsik; Jung, Myunggi; Ha, Min Woo; Lee, Myungmo; Park, Yohan; Kim, Mi-hyun; Kim, Taek-Soo; Lee, Jihoon; Park, Hyeung-geun

doi:10.1039/c3ob42107d

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Enantioselective synthesis of α-halo-α-alkylmalonates via phase-transfer catalytic α-alkylation : Enantioselective synthesis of alpha-halo-alpha-alkylmalonates via phase-transfer catalytic alpha-alkylation

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Authors: Hong, Suckchang; Kim, Minsik; Jung, Myunggi; Ha, Min Woo; Lee, Myungmo; Park, Yohan; Kim, Mi-hyun; Kim, Taek-Soo; Lee, Jihoon; Park, Hyeung-geun

Issue Date: 2014-03

Publisher: Royal Society of Chemistry

Citation: Organic and Biomolecular Chemistry, Vol.12 No.9, pp.1510-1517

Abstract: A new enantioselective synthetic method for alpha-halo-alpha-alkylmalonates is reported. alpha-Alkylation of diphenylmethyl tert-butyl alpha-halomalonates under phase-transfer catalytic conditions (solid KOH, toluene, -40 degrees C) in the presence of (S,S)-3,4,5-trifluorophenyl-NAS bromide (5 mol%) afforded diphenylmethyl tert-butyl alpha-halo-alpha-alkylmalonates in very high chemical yields (up to 99%) and optical yields (up to 93% ee).