October 2013
Intermediate to advanced
242 pages
9h 22m
English
Content preview from Methods of Non-a-Amino Acid Synthesis, 2nd Edition
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195Aminocyclic andHeterocyclic Amino Acids
N,N-dialkylamino derivatives were prepared by using different enamines of
isobutyraldehyde.
NMe
2
Me
2
N CO
2
Me
CH
2
=CHCO
2
Me
175°C, 2 h
153 154
75%
There are cycloaddition processes that do not necessarily involve pericyclic reac-
tions. A three-component cycloaddition strategy was used to prepare functionalized
aminocyclohexanecarboxylic acids. The reaction of 155 with ethyl 3-oxobutanoate
and an amine such as butylamine, in the presence of ceric ammonium nitrate, led to
156 in 77% yield.
110
Subsequent reduction with an acyloxyborohydide gave 157 in 94%
yield. Several derivatives were prepared by this method u ...
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