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Organocatalytic Nitroaldol Reaction Associated with Deuterium‐Labeling
Author(s) -
Yamada Tsuyoshi,
Kuwata Marina,
Takakura Ryoya,
Monguchi Yasunari,
Sajiki Hironao,
Sawama Yoshinari
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201701224
Subject(s) - nitromethane , chemistry , deuterium , electrophile , nitroaldol reaction , organocatalysis , oxide , organic chemistry , catalysis , combinatorial chemistry , enantioselective synthesis , physics , quantum mechanics
A deuterium‐labeling reaction of nitroalkanes in deuterium oxide and the subsequent nitroaldol reaction have been accomplished under basic and organocatalytic conditions to provide the deuterium‐labeled β ‐nitroalcohols in high yields and high deuterium contents. β ‐Deuterated β ‐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 α ‐keto esters as electrophiles in the presence of a quinine‐derived organocatalyst in deuterium oxide could provide the desired β ‐deuterated nitroalcohol derivatives with high enantioselectivities.