TRANSITION METAL -CATALYZED HOMOGENEOUS ASYMMETRIC HYDROGENATION - Catalytic Asymmetric Synthesis - page 359

TABLE 7.1. ( Continued )

% ee
(Confi g.) Ligand R 1 R 2 S / C Reaction Conditions a Reference

( R,R ) - NORPHOS Ph H 95 MeOH, rt, 1.1 atm 96 ( S ) 6 7

ClickFerroPhos Ph H 100 MeOH/toluene 1 : 1,

1 atm

99 ( R ) 5 1

Et - 35 Ph H 100 MeOH, rt, 3 atm > 99 ( S ) 6 8

( S,S ) - FerroPhos Ph H 100 EtOH, rt, 2 atm 98.9 ( R ) 6 9

( − ) - BIPNOR Ph H 100 EtOH, rt, 3 atm > 98 ( S ) 7 0

( R ) - 47 Ph H 100 MeOH, rt, 3.3 atm > 99 ( R ) 4 9

116 Ph H 1,000 THF, rt, 2 atm 99.0 ( S ) 7 1

( R ) - SpiroP Ph H 100 MeOH, rt, 1 atm 97.9 ( R ) 7 2

( R,R ) - DIPAMP Ph Me 900 MeOH, 50 ° C, 3 atm 96 ( S ) 7 3

112 Ph Me 100 CH 2 Cl 2 , rt, 1 atm > 99.9 ( R ) 7 4

( R,R ) - Ph - BPM Ph Me 3,000 MeOH, 30 ° C, 10 bar 99 ( S ) 4 5

( S,S ) - Quinox Ph Me 1,000 MeOH, 30 ° C, 10 bar 99.5 ( R ) 5 3

Ph Me 50,000 MeOH, rt, 61 atm 7 5

( R,R ) - PYRPHOS 96.5 ( S )

Ph Me 100 EtOH, rt, 3 atm 1 5

( S ) - BINAP 100 ( S )

Ph Me 1,000 EtOH, rt, 1 atm 7 7

( R ) - BICHEP 95 ( S )

28 Ph Me 100 MeOH, rt, 1 atm 7 8

98.4 ( S )

( R,R,R ) - 22 Ph Me 1,000 MeOH, 25 ° C, 2 atm 98 ( R ) 7 9

( R ) - ( S ) - JosiPhos Ph Me 100 MeOH, 35 ° C, 1 atm 96 ( S ) 8 0

( R ) - ( S ) - 84 Ph Me 100 MeOH, rt, 1 atm 98.0 ( S ) 8 1

92 Ph Me 100 MeOH/toluene,

1 atm

96.6 ( R ) 8 2

( S,S ) - 41 Ph Me 500 MeOH, rt, 2 atm 99.2 ( R ) 8 3

( S,S,R,R ) -
TangPhos

Ph Me 10,000 MeOH, rt, 1.3 atm 99.8 ( S ) 8 4

i Pr - BeePhos

Ph Me 200 MeOH, 30 ° C, 4 atm 98 ( R ) 8 5

123 Ph Me 100 THF, rt, 7.8 atm 97 ( S ) 8 6

124 Ph Me 100 THF, rt, 1.0 atm 97 ( R ) 8 6

( S re, R c) - 125 Ph Me 500 MeOH, 30 ° C, 4 atm 97 ( R ) 8 7

119 Ph Me 100 H 2 O, rt, 5 atm 99.9 ( S ) 8 8

121 Ph Me 100 CH 2 Cl 2 , 25 ° C, 5 atm 98 ( S ) 8 9

(1 R , 2 S ) - DIPAMP Ph Me 10,000 MeOH, rt, 3.3 atm 97 ( R ) 90a

( S ) - Xyl - BDPAB Ph Me 500 MeOH, rt, 3.3 atm 98 ( S ) 9 1

98 Ph Me 10,000 THF, rt, 10 psi 99.4 ( S ) 9 2

( S C , R P , S a ) - 103 Ph Me 100 CH 2 Cl 2 , rt, 10 atm 99.0 ( R ) 9 3

( S ) - 54 Ph Me 400 THF, rt, 20 atm 97.4 ( R ) 6 6

( S ) - SIPHOS Ph Me 200 CH 2 Cl 2 , rt, 1 atm 96.4 ( S ) 94a

( S ) - 56 Ph Me 100 Toluene, rt, 10 atm 99 ( S ) 9 5

( R ) - 55 Ph Me 100 rt, 1.7 atm 98.4 ( S ) 9 6

a Complete conversion unless otherwise noted.