Page 830 - Advanced Organic Chemistry Part B - Reactions & Synthesis

806 Scheme 9.3. Addition Reactions of Allylic Boranes and Carbonyl Compounds

CHAPTER 9 1 a O OH
Carbon-Carbon CH 3 CH 2 B –78°C
Bond-Forming Reactions O + PhCH O Ph
of Compounds of Boron,
Silicon, and Tin H H CH 3
diastereoselectivity >95%

2 a O OH
H CH 2 B –78°C
O + PhCH O Ph
CH 3 H CH
3
diastereoselectivity >95%
3 b H H O CH 3 O
O + O CH
O O
CH 3 CH B
2
O OH 91%
4 c CH 3
O
CO CH 3
2
2
3
B CH 3 + CH CCO CH 3 96% yield,
CH 3 OH 73:27 anti-syn mixture
3 3
5 d Si(CH )
CH 3
B CH H C H Si(CH )
3 3
4 9
+ C H CH O
4 9
H CH 3 OH 63%; 4% syn-isomer
6 e
O O
CH 3 O
O + Z- CH OCH CHCH B(OCH )
O CH 3 2 3 2 O
83%
CH 3 OH CH 3
7 f HO
CH O –95°C
+ Z- ClCH CHCH B
2
Cl 57%
8 g Cl OH
Ph CH O O Ph
+ B
CH Cl
CH CH 3 3 O CH CH 3 CH 3
3
3
58%
9 h OH
) BCH CH CH 2 + PhCH O
2
2
( Ph
95% e.e.
(Continued)