Journal
ORGANIC LETTERS
Volume 23, Issue 4, Pages 1516-1520Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c00314
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Funding
- National Research Foundation of Korea (NRF) - Korean Government (MSIT) [NRF-2019R1A4A2001440, 2019R1A2C2087018]
- 111 Project [D18012]
- National Research Foundation of Korea [2019R1A2C2087018] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
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A catalytic enantioselective acyloin rearrangement is utilized to synthesize highly optically active acyloin derivatives, yielding chiral alpha-hydroxy aryl ketones and chiral alpha-siloxy alkyl ketones with high yields and good enantioselectivity.
A catalytic enantioselective acyloin rearrangement of acyclic aldehydes to synthesize highly optically active acyloin derivatives is described. In the presence of a chiral oxazabor-olidinium ion catalyst, the reaction provided chiral alpha-hydroxy aryl ketones in high yield (up to 95%) and enantioselectivity (up to 98% ee). In addition, the enantioselective acyloin rearrangement of alpha,alpha-dialkyl-alpha-siloxy aldehydes produced chiral alpha-siloxy alkyl ketones in high yield (up to 92%) with good enantioselectivity (up to 89% ee).
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