Chemistry Reference
In-Depth Information
3.2.5 Neopentane-Based
The O
2
NC[(CH
2
)
3
OH]
3
was protected (C
6
H
5
CH
2
Cl) to give O
2
NC-
[(CH
2
)
3
OCH
2
Bn]
3
, which underwent denitration-cyanoethylation [82] upon treat-
ment with n-Bu
3
SnH and AIBN in the presence of acrylonitrile generating interme-
diate NCCH
2
CH
2
C[(CH
2
)
3
OH]
3
, which was hydrolyzed to HO
2
CCH
2
CH
2
C-
[(CH
2
)
3
OH]
3
[83,84].
CHCN was converted to OHCC(CH
2
CH
2
CN)
3
, which
was reduced and protected giving TBSOCH
2
C(CH
2
CH
2
CN)
3
; then reduction of the
cyano groups (RaNi, H
2
NNH
2
) gave TBSOCH
2
C[(CH
2
)
3
NH
2
]
3
, which was ami-
dated, deprotected, and oxidized (Jones) forming HO
2
CC[(CH
2
)
3
NHCOR]
3
[85,86].
Acetaldehyde with CH
2
ΒΌ
3.2.6 ArylC-Based
