Page 412 - Advanced Organic Chemistry Part B - Reactions & Synthesis

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Scheme 5.3. Enantioselectivity for Catalytic Hydrogenation of Substituted
Acrylic Acids SECTION 5.1
Addition of Hydrogen at
Reactant Catalyst Product Configuration % e.e.
Carbon-Carbon Multiple
Bonds
1 a
CO 2 H H
Ph 2 CH 3 CHCO 2 H R 90
C P
CH 2 CH 3
Rh
P
NHCCH 3 CH 3 NHCCH 3
Ph 2 H
O O
2 a CO 2 H
H PhCH 2 CHCO 2 H S 95
C C Same as above
Ph NHCCH 3
NHCCH 3
O
O
CH 3 O
b 94
3 H CO 2 H PhCH 2 CHCO 2 H R
C C
NHCCH 3
Ph P
NHCCH 3
Rh O
O P
OCH 3
4 c
H CO 2 H
C C PhCH 2 CHCO 2 H S 100
PPh 2
Ph NHCPh Rh
PPh 2 NHCPh
O
O
5 d
CO 2 CH 3 99.2
CO 2 CH 3 R
C 2 H 5
H 5 C 2
CH 3 CH 3
P
NHCCH 3
Rh NHCCH 3
O P O
H 5 C 2
C 2 H 5
CH 3 O
6 b
H CO 2 C 2 H 5 PhCH 2 CHCO 2 C 2 H 5 S 90
P
C C Rh O 2 CCH 3
Ph O 2 CCH 3 P
OCH 3
CH 3 O
7 e
CO 2 CH 3 R 88
CH 3 CH 2 CO 2 CH 3
C
CH 2
CH 2 CO 2 CH 3
CH 2 CO 2 CH 3 P
Rh
P
OCH 3
8 f C 2 H 5
H 5 C 2
(CH 3 ) 2 CH P (CH 3 ) 2 CH R 99
CH Rh CH 2
P
CO 2 H CO 2 H
CH 3 O 2 C H 5 C 2 C 2 H 5 CH 3 O 2 C
(Continued)