Page 163 - Advanced Organic Chemistry Part B - Reactions & Synthesis

Scheme 2.10. Intramolecular Aldol and Mukaiyama Aldol Reactions 135

CHO SECTION 2.1
H O
2
1 a Aldol Addition and
O CH(CH 2 ) 3 CHCH O Condensation Reactions
115°C
C 3 H 7
C 3 H 7
O
2 b HO –
CH 3 CH 2 CH CHCH 2 CH 2 CCH 2 CH 2 CH O CH 3 CH 2 CH CHCH 2
O
73%
3 c O O
HO
NaOH
N O
CH 3 N O
CH 3
CH 3 C 80%
O
H H
4 d CH 3 O CH 3 O OH
NaOCH 3
O O
CH 2 CH O
R 3 SiO H 3 C R 3 SiO H 3 C 63%
5 e CH 3 CH 3
O
NaOCH 3 CH 3 CH 3
O
CH 3
CH 3
CH 3 HO 66%
O
6 f CH 3 HO CH 3 O
O
O CHCH 2 H 3 C
H 3 C
DBU
CH 3
CH 3
OTMS
OTMS H
H CH 3 O 2 C 65–70%
CH 3 O 2 C
7 g TMSO O
CH 2
ZnCl 2
CH(OCH 3 ) 2 OCH 3
H H H H 59%
CH 3 CH 3
CH 3 CH 3

C 2 H 5 O 2 C CO 2 C 2 H 2 O
OTMS
8 h Zn 2 Cl 2
(CH 3 O) 2 CH CH 3 O
or
CH 3 O 2 C CO 2 CH 3
TiCl 4 40–60%
(Continued)