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Indium‐Mediated Aza‐Henry Reaction of Imines: Access to 2‐Nitroamines
Author(s) -
Soengas Raquel G.,
Silva Sandrina,
Estévez Amalia M.,
Estévez Juan C.,
Estévez Ramón J.,
RodríguezSolla Humberto
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201200304
Subject(s) - indium , chemistry , nitroethane , reaction conditions , organic chemistry , medicinal chemistry , catalysis
A new method has been developed to obtain 2‐nitroamines by an indium‐promoted reaction of bromonitromethane with a variety of imines. On the strength of these results, the reaction was also performed with 2‐bromo‐2‐nitropropanes to afford 2,2‐dialkyl‐2‐nitroamines. Moreover, the indium‐mediated reaction of 1‐bromo‐1‐nitroethane and imines afforded 1‐methyl‐2‐nitroamines with remarkably high anti selectivity. The use of chiral sugar‐derived imines furnished the corresponding 2‐nitroamines with excellent stereoselectivity.