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Highly enantioselective synthesis of α,α-dialkylmalonates by phase-transfer catalytic desymmetrization : Highly enantioselective synthesis of alpha,alpha-dialkylmalonates by phase-transfer catalytic desynnmetrization
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Cited 51 time in Scopus
- Authors
- Issue Date
- 2011-04
- Publisher
- American Chemical Society
- Citation
- Journal of the American Chemical Society, Vol.133 No.13, pp.4924-4929
- Abstract
- A novel enantioselective synthetic method for the construction of a quaternary carbon center from malonates via phase-transfer catalytic (PTC) alkylation has been developed. The asymmetric alpha-alkylation of diphenylmethyl tertbutyl alpha-alkylmalonates with alkylating agents under phase-transfer catalysis conditions (aq 50% KOH, toluene, 0 degrees C) in the presence of (S,S)-3,4,5-trifluorophenyl-NAS bromide (8) as PTC catalyst afforded the corresponding alpha,alpha-dialkylmalonates in high chemical (up to 99%) and optical yields (up to 97% ee) which could be readily converted to versatile chiral intermediates. Notably, the direct double alpha-alkylations of diphenylmethyl tert-butyl malonate also provided the corresponding alpha,alpha-dialkylmalonates without loss of enantioselectivity. The synthetic potential of this method has been demonstrated by the preparation of alpha,alpha-dialkylamino acid and oxindole systems.
- ISSN
- 0002-7863
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