Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 360, Issue 4, Pages 637-641Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201701224
Keywords
deuterium-labeling; deuterium oxide; enantioselectivity; organocatalysis; nitroaldol reaction
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Funding
- Japan Society for the Promotion of Science [JSPS: 16K08169]
- JSPS [15J01556]
- Grants-in-Aid for Scientific Research [15J01556, 16K08169] Funding Source: KAKEN
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A deuterium-labeling reaction of nitro-alkanes in deuterium oxide and the subsequent nitroaldol reaction have been accomplished under basic and organocatalytic conditions to provide the deuterium-labeled beta-nitroalcohols in high yields and high deuterium contents. beta-Deuterated beta-nitroalcohols could be smoothly obtained from the reaction of nitroalkanes and various electrophiles using the easily-removal basic resin WA30. Furthermore, the asymmetric nitroaldol reaction using nitromethane and alpha-keto esters as electrophiles in the presence of a quinine-derived organocatalyst in deuterium oxide could provide the desired beta-deuterated nitroalcohol derivatives with high enantioselectivities.
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