Page 422 - Advanced Organic Chemistry Part B - Reactions & Synthesis

Scheme 5.5. Enantioselective Hydrogenation with Ruthenium Complex Catalysts 395

1 a OH SECTION 5.2
O
Ru(BINAP)Cl 2 CO C H
C H 2 2 5 Catalytic Hydrogenation
CO 2 2 5
800 psi H 2 of Carbonyl and Other
30°C 95% yield Functional Groups
Cl Cl
98% e.e.
2 b O O Ru(BINAP)Cl 2 OH O
200 psi H
Ph NHCH 3 100°C 2 Ph NHCH 50% yield
3
100% e.e.
3 c S CH 3
S CH 3
CH 3 Ru(BINAP)Br 2 CH 3 CO C H 5
2
2
CO 2 C H
2 5 H 2
O OH 50% yield
83% e.e.
4 d O OH
O O
cat E
C H CO C H
CO 2 2 5
TESO (CH ) CHOH TESO 2 2 5
3 2
100%
92:8 dr
5 e CH 3 CH 3 cat D CH 3 CH 3
OH
O O O
O O HCO 2 H, O O
N
CH 3 Et 3 CH 3
95% , single
stereoisomer
6 f O cat E OH
C H 7 C H
3
CH (CH ) CHOH 3 7 CH
3 3 2 3 60% yield,
> 95% e.e.
7 g O OH
OTES OTES
cat E
OTBS OTBS
TESO (CH ) CHOH TESO
CH 3 3 2 CH
CH 3 CH 3 CH CH 3 3 85%
3
8 h CH 3 CH 3 CH 3 CH 3 OH
O O cat E O
O O (CH ) CHOH O O
O ) 3 2 O Si(CH )
CH Si(CH 3 3 CH 3 3
3 3
49%
> 97% ds
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