Phase-transfer catalyzed enantioselective α-alkylation of α-acyloxymalonates: construction of chiral α-hydroxy quaternary stereogenic centers
- Phase-transfer catalyzed enantioselective α-alkylation of α-acyloxymalonates: construction of chiral α-hydroxy quaternary stereogenic centers
- 이재균; 하민우; 최수지; 김식; 이준영; 이지연; 홍석창; 박형근
- chiral a-hydroxy; x-ray crystal; enantioselective
- Issue Date
- RSC advances
- VOL 6, NO 81-77430
- The enantioselective synthesis of α-acyloxy-α-alkylmalonates was developed as an efficient method for producing chiral α-tertiary alcohols, which are potentially valuable intermediates in the synthesis of natural products and pharmaceuticals. The efficient enantioselective α-alkylation of diphenylmethyl tert-butyl α-acyloxymalonates was accomplished via phase-transfer catalysis in the presence of (S,S)-3,4,5-trifluorophenyl-NAS bromide to afford the corresponding α-acyloxy-α-alkylmalonates at high chemical (up to 99%) and optical (up to 93% ee) yields, which could be readily converted to versatile chiral intermediates with a chiral α-tertiary alcohol group.
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