Strem Chemicals, Inc.

Strem Chemicals, Inc.
www.strem.com
Catalog # 15-0473
(-)-1,2-Bis((2R,5R)-2,5-diphenylphospholano)ethane, min. 98% (R,R)-Ph-BPE
P
P
Note: Manufactured under US Patent 5,021,131 and US Patent 5,171,892.
Technical Notes:
1. Phenyl-BPE exhibits enhanced activity and selectivity over existing members of the BPE ligand family in rhodium catalysed
asymmetric hydrogenation.
2. This ligand is highly efficient for the hydrogenation of N-acyl aryl-enamides.
3. Molar substrate/catalyst ratios of up to 100,000/1 are achieved with excellent reactivity and enantioselectivity using
commercial grade substrates and solvents.
4. Ligand in the rhodium-catalyzed asymmetric hydroformylation of olefins.
5. Ligand for asymmetric addition of allyl cyanide to ketones.
6. Ligand for catalytic enantio- and diastereoselective aldol reaction of thioamides.
[(R,R)-Ph-BPE Rh (COD)]BF 4
S/C 100,000
CO
MeO 2 C
2 Me
CO
MeO 2 C
2 Me
10 bar H 2 , MeOH, 25 o Ref. (1)
C
100% conversion
99% ee
Ph
CO 2 Me
NHAc
[(R,R)-Ph-BPE Rh (COD)]BF 4
S/C 3000
10 bar H 2 , MeOH, 28 o C
CO 2 Me
Ph NHAc
100% conversion
99% ee
Ref. (1)
Ar
NHAc
[(S,S)-Ph-BPE Rh (COD)]BF 4
S/C 5000-1000
10 bar H 2 , MeOH, 25 o C
Ar
NHAc
Ref. (2)
CHO
98-99% ee
R
Rh catalyst
CO/H 2
R
Tech. Note (4)
Ref. (3)
O
[Cu(CH 3 CN) 4 ]ClO 4
P
(R,R)-Ph-BPE +
Ph Ph
Li(OC 6 H 4 p-OMe)
P Ph
OH
Ph R
O
0.5-5 mol %
1
O
CN
R 1
+
THF, -40
R 1 R o C
CN
2
yield up to 90%
up to >99% ee
Tech. Note (5)
Ref. (4)
R 1
O
H
S
+
H
R 2
NR 3 2
[Cu(CH 3 CN) 4 ]PF 6
(R,R)-Ph-BPE
LiO
+
3 mol %
DMF, -60 o C
O
OH
S
R 1
R 2
63-96%
88-97% ee
NR 3 2
Tech. Note (6)
Ref. (5)

References:
1. Org. Lett., 2003, 5, 1273.
2. Tetrahedron Lett., 2004, 45, 9277.
3. Angew. Chem. Int. Ed., 2005, 44, 5834.
4. J. Am. Chem. Soc., 2010, 132, 5522.
5. J. Am. Chem. Soc., 2011, 133, 5554.