Improved Methodology for the Preparation of Chiral Amines

Table 1.1 Rhodium Catalyzed Reduction of Enamide
Substrate Ligand H 2 (bar) ee Configuration
R = H, Ar = Ph Manniphos R=
Me
10 99.5 (R)
R = H, Ar = p-CF 3 Ph Tangphos 1.4 99 (R)
R = H, Ar = p-NO 2 Ph DiSquare P* 2 99 (R)
R = H, Ar = p-ClPh MorPhos 55 99 (R)
R = H, Ar = Ph Aaphos 10 87 (R)
R = H, Ar = Ph (17) 10 93 (R)
R = H, Ar = m-CO 2 MePh t-Bu-BisP* 3 97 (S)
R = H, Ar = Ph (18) 20.6 96.5 (S)
F 3 C CF 3
Ph
O
Fe
O
P CF 3
OR
O
P P
N
O P
O
O
PPh 2 CF 3
Ph O
DiSquare P*
ManniPHOS
17
H O
PR
N P
2 O
O
O P N O PPh 2
PPh 2
Re
CO
Fe
OC CO
AaPHOS (R = Cy)
MorPHOS 18
Figure 1.9. Examples of Different Ligands Used in Enamide Reduction.
27