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Issue 81, 2016, Issue in Progress
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Phase-transfer catalyzed enantioselective α-alkylation of α-acyloxymalonates: construction of chiral α-hydroxy quaternary stereogenic centers

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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.

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

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Article information


Submitted
10 Jun 2016
Accepted
03 Aug 2016
First published
09 Aug 2016

RSC Adv., 2016,6, 77427-77430
Article type
Communication

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

M. W. Ha, S. Choi, S. Kim, J. Y. Lee, J. K. Lee, J. Lee, S. Hong and H. Park, RSC Adv., 2016, 6, 77427
DOI: 10.1039/C6RA15121C

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