Page 141 - Catalysts for Fine Chemical Synthesis Vol 1 - Robert & Poignant
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128 hydrolysis, oxidation and reduction
Table 9.2 Asymmetric hydrogenation of keto esters with BisP*±Ru(II)
catalysts.
Entry Substrate BisP* Product Yield(%) % ee
O O OH O
1 a 86 97
OMe OMe
2 b) O O a OH O 96 98
OMe OMe
3 b 18 87
O O OH O
4 O a O 100 81
OMe OMe
O O OH O
5 OMe a OMe 81 98
O O OH O (syn) 13 91
6 c) OMe a * OMe (anti) 70 96
O O OH O (syn) 39 96
7 OEt a * OEt (anti) 45 97
O O OHO
8 OEt a OEt 100 89
O OH
OMe OMe
9 a 90 70
O O
O OH
OEt OEt
10 a 77 50
O O
O OH
11 OEt a OEt No reaction
O O
O O OH O
12 a No reaction
OEt OEt
O O OH O
13 d) a 100 89
NH 2 NH 2
O O OH O
14 e) a 51 85
P(OMe) 2
P(OMe) 2
2
a) Reaction conditions: substrate 2 mmol, catalyst/substrate 0.005, 70 8C, 6 kg/cm .
b) Substrate 82 mmol, catalyst/substrate 0.0013.
c) At 50 8C.
d) Substrate 0.7 mmol, catalyst/substrate 0.014, at 50 8C.
e) At 60 8C.
