Phase-transfer catalyzed enantioselective α-alkylation of α-acyloxymalonates: construction of chiral α-hydroxy quaternary stereogenic centers

Title
Phase-transfer catalyzed enantioselective α-alkylation of α-acyloxymalonates: construction of chiral α-hydroxy quaternary stereogenic centers
Authors
이재균하민우최수지김식이준영이지연홍석창박형근
Keywords
chiral a-hydroxy; x-ray crystal; enantioselective
Issue Date
2016-11
Publisher
RSC advances
Citation
VOL 6, NO 81-77430
Abstract
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.
URI
http://pubs.kist.re.kr/handle/201004/64814
ISSN
2046-2069
Appears in Collections:
KIST Publication > Article
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