
36
Methods of Non-α-Amino Acid Synthesis, Second Edition
catalysis method allowed an amine to add to an alkene in an anti-Markovnikov manner,
as shown, rather than the Markovnikov addition observed in the formation of 138.
(CH
2
)8
O
HO
(CH
2
)
8
O
NHn-
2
2
130°C, H
2
O . p-TsOH
Rh(acac)(CO)
2
–
Ru(acac)
3
/22'bipy
200 201
65%
A formal oxidative addition with weak nucleophiles such as amides is possible if
radical conditions are used.
179
The reaction of N-butyl acetamide and methylpent-4-
enoate, in the presence of di-tert-butyl peroxide at 160°C, gave methyl 5-(N-acetyl-N-
butylamino)pentanoate, 202.
179
A limitation to this approach is that only one al ...