Page 164 - Catalysts for Fine Chemical Synthesis Vol 1 - Robert & Poignant
P. 164
asymmetric reduction using nonmetallic catalysts 151
Table 11.2 Reduction of aromatic ketones using oxazaphosphinamide catalyst [13]
(results according to the literature).
Yield % ee %
O
CH 3 89 90
H 3 CO
O
82 90
CH 3
O
X Cl X = H; 8 94
X = CH 2 OBn; 93
BnO 84
O
83 >90
O
O
71 >90
O
11.4 ASYMMETRIC REDUCTION OF CHLOROACETOPHENONE
USING A SULFOXIMINE CATALYST [S]
11.4.1 PREPARATION OF b-HYDROXYSULFOXIMINE BORANE
O NH BSA,CH 3 CN O NSiMe 3 n-BuLi NH HO
O Ar
S S S
Ph CH 3 50 8C Ph CH 3 O Ar
Ph
Ar Ar
Materials and equipment
. (SS)-Methyl-S-phenylsulfoximine, 523 mg, 3.4 mmol*
* (SS)-Methyl-S-phenylsulfoximine was kindly provided by Prof. C. Bolm (Technische RWTH
Aachen)
