Page 376 - Advanced Organic Chemistry Part B - Reactions & Synthesis

348 Scheme 4.9. Synthesis of Alcohols, Aldehydes, Ketones, and Amines from
Organoboranes
CHAPTER 4
A. Alcohols
Electrophilic Additions
to Carbon-Carbon 1 a
Multiple Bonds CH 3 H C H
3
1)B H 6 OH
2
–
2)H O , OH
2
2
85%
2 b
1) B H 6 H
CH 2 2 CH OH
2
–
CH 3 2) H 2 O , OH CH 3
2
CH 3 CH 3
76%
3 c CH 3 CH 3
H
1) B H OH
2 6
–
2) H O , OH 85%
2
2
4 d
OH
H CH OCH Ph
2
2
1) B H , THF CH OCH Ph
2 6
CH 2 2
O 3 2) H O , OH O
–
H CH 3 2 2 CH 3 CH 3 85%
B. Ketones and aldehydes
5 e Ph
CH 3 1) B H CH 3 Ph
2 6
C
CH 3 2) CrO 3 CH
H 3 O 50%
6 f
1) BH /S(CH ) O
3 2
3
2) N-methylmorpholine-
+
N-oxide, R N RuO 4 –
4
7 g CH 3 H
CH 3 H CH OAc
disiamylborane 2
CH OAc
2
pyridinium
chlorochromate CH CH O
2
CH CH 2 H 80%
H
C. Amines
8 h
CH 3 CH 3
1) B H NH 2
2 6
2) H NOSO H
2
3
42%
9 i
1) BHCl 2
NHPh
2) PhN , H O 84%
3
2
(Continued)