Page 853 - Advanced Organic Chemistry Part B - Reactions & Synthesis

Scheme 9.4. (Continued) 829

j CH 3 SECTION 9.2
10 CH 3 Si(CH 3 ) 3 H
BF 3
OC 2 H 5 Organosilicon
+ CH O Compounds
O 3 –78°C
CH
) MOMO 3
MOMO H TBBMSO CH(CH 3 2 H CH(CH )
3 2
TBDMSO 79%
C. Reactions with Iminium ions
CF CO 2 H
11 k 3
O N OH O N
CH CH CH CHSi(CH )
3 3
2
2
91%
12 l O O
O O
CO H
CF 3 2
(CH ) SiCH CH(CH ) 2
2
3 3
N N 73%
H
H
13 m
OTIPS OTIPS
Si(CH ) BF
3 3
CH + OTIPS 3 OTIPS
5
2
C H 19 2 C H O N C H CH CHCH 2 N
9
19
9
CO C(CH ) C(CH )
2 3 3 CO 2
3 3
D. Acylation reactions
14 n
H O
TiCl CH CH
C + CH CCl 4 2
3
CH Si(CH ) CCH 3
2 3 3 82%
O
15 o CH Si(CH )
2
3 3
O O
CH 2
, 90°C
+ CH CCl AlCl 3 CCH
3 3
50%
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