Details

Item Description Structure
Catalog 8173 CAS 158923-07-0
Product Name (S)-(+)-1-[(R)-2-(Dicyclohexylphosphino)ferrocenyl]ethyldicyclohexylphosphine
Other Name NA
Purity 97% ee 99%
Molecular Formula C36H56FeP2
Molecular Weight 606.64
Color and Form orange
Package 5g/10g and more Bulk Ordering Package
Solubility NA
Melting point NA
Stability Yes
Risk R20/22... Safety S26/S45 Hazard NA
spectrometry Conforms to structure
HPLC Conforms to structure
Note Only for research purposes only
Technical Note
Technical Notes:
Ferrocenylphosphine ligands of the type cpFecp(PR2)(*CH(CH3)PR'2) are a class of asymmetric ligands developed at Solvias in Basel, Switzerland. Ligands of this type are currently used industrially in the stereoselective synthesis of commercial products. A unique feature of these bidentate ligands is the presence of a fixed phosphine moiety and a stereogenic, functionalized side chain, which can be easily modified to accommodate electronic and steric requirements. Based on a versatile synthetic procedure starting with optically active ferrocenes of the type cpFecp(PR2)(*CH(CH3)X) [X = OAc or NR2], a variety of donor atoms can be introduced into the side chain.These ferrocene based phosphine ligands have wide application in the stereoselective hydrogenation of substituted acetamidoacrylates, enol acetates, -ketoesters and simple
alkenes.
Useful as a ligand in Pd-catalyzed C-N bond-forming reactions.
Pd-catalyzed enantioselective alkylative desymmetrization of meso-succinic anhydrides.
Asymmetric hydrogenation of ketones and phosphinylketimines.
Michael addition of Grignard reagents to ",$-unsaturated esters and thioesters.
Boration of ",$-unsaturated esters and nitriles.
Reaction of aryl halides with ammonia.
Cu-catalyzed reduction of activated C=C bonds with PMHS.
Regio- and enantioselective hydroboration of vinyl arenes.
Rh-catalyzed asymmetric ring-opening reactions of oxabicyclic alkenes.
1,2-Migrations in Pd-catalyzed Negishi couplings with JosiPhos ligands.
References:
1. Solvias owns the patent rights for Strem products 26-1000, 26-1001, 26-1200, 26-1201, 26-1230,
26-1101, and for the Ir and Rh complexes of the aforementioned products, including the
complexes of 26-1210 and 26-1211.
2. C&E News, July 22, 1996, 38.
3. Angew. Chem. Int Ed., 1996, 35, 1475.
4. J. Org. Chem., 1972, 37, 3052.
5. J. Am. Chem. Soc., 1994, 116, 4062.
6. Inorg. Chim. Acta., 1994, 222, 213.
7. Organometallics, 1996, 15, 860.
8. Helv. Chim. Acta., 1995, 78, 883.
9. European Patents; EP 624587 A2 941117, EP 612758 A1 940831, EP 564406 A1 931006.
10. Comprehensive Asymmetric Catalysis, 1999, Chapter 6.1, pg. 199-207.
11. Topics in Catalysis, March 2002, 19. (review)
12. J. Am. Chem. Soc., 2004, 126, 10248.
13. (a) Angew. Chem. Int. Ed,, 2007, 46, 7651. (b) Adv. Synth. Catal., 2002, 343, 68.
14. Angew. Chem. Int. Ed., 2005, 44, 2752.
15. Angew. Chem. Int. Ed., 2007, 47, 145.
16. J. Am. Chem. Soc., 2006, 128, 10028.
17. (a) Angew. Chem. Int. Ed., 2003, 42, 4793. (b) Angew. Chem. Int. Ed., 2006, 45, 2785.
(c) J. Am. Chem. Soc., 2009, 131, 10386.
18. Angew. Chem. Int. Ed., 2006, 45, 17674. (review)
19. J. Am. Chem. Soc., 2004, 126, 9200.
20. Proc. Natl. Acad. Sci. U.S.A., 2004, 101, 5455.
21. J. Org. Chem., 2009, 74, 135.
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Products under Patent are not for ultimate sale in the country where patent has not expired. All liability for violation of Patent laws will be to the account of the Purchaser.
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