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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11Functional Group Exchanges
reacted with ethyl acetoacetate to give 56 in 73% yield.
58
One modication used
a mixture of ammonia and p-toluenesulfonic acid to induce the reaction.
59
Such
enamino derivatives are actually 3-aminobutenoic acid derivatives and can be used
as such or reduced to 3-aminobutenoic acid derivatives.
CO
2
Et
O
CO
2
Et
NH
2
54 55
NH
3
CO
2
Et
NMe
2
CO
2
Et
O
56
82%
NHMe
2
This approach can be used to prepare many substituted alkene-amino acid deriva-
tives from an appropriate β-keto-ester.
60
The reaction of ethyl 4-methyl-3-oxopen-
tanoate with ammonia in ethanol gave ethyl 3-amino-4-methylpent-2-enoate in 75%
yield.
61
Diketo-ester 57 reacted with ...
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