Page 831 - Advanced Organic Chemistry Part B - Reactions & Synthesis

Scheme 9.3. (Continued) 807

10 i CH CH 3 SECTION 9.1
3
OH
BCH O O Organoboron
(Ipc) 2 2 H CH 3 Compounds
+ O CH O CH 3 O
H Ph Ph
96:4 diastereoselectivity,
89% e.e.
11 j i - PrO C
2 O O
CH CH + O O
BCH 2 2
O O
i - PrO C O CH OH 91% yield
2
96:4 diastereoselectivity
- i - Pr
12 k CO 2
CO i Pr OH
O 2
BO
) CH
CH + O CH(CH 2 4 3 (CH 2 ) 4 CH 3
3
CH 3 C H
CH 3 2 5
73% e.e.
13 l CO C H 5 OH
2
2
TBDPSO CH O O TBDPSO
+
O B C H O
O CO 2 2 5
95% yield, > 96% e.e.
14 m OTBDMS O
CH O
PhCH O + TBDMSO B
2
O
OCH 3
TBDMSO OH
OTBDMS
PhCH O
2
OCH CH CH
3 2
85% total yield,
major isomer of mixture
15 n OCH 3 OH
3 2
(Ipc) 2 B + O CHCH(CH )
ethanolamine 57% yield,
CH O 100% anti, 88% e.e.
3
16 o
–100°C
+ O CH SO 2 Ph SO 2 Ph
(Ipc) B OH
2
62% yield, 86% e.e.
17 p OH
O CH
+
(Ipc) 2 B OTPS OTPS
NHCO C(CH )
C(CH ) 2 3 3
3 3
NHCO 2
18 q OCH 3
HO O
OMEM O
B + O OH
O
(Ipc) 2
OH O
87% >98% e.e.
19 r CO 2 CH OH
O CH 3 CO CH 3
2
CH(CH 3 ) 2 CH(CH )
(Ipc) B CH 3 + O O 3 2
2
N
N
CH 3
Ph Ph 70%
(Continued)