Details

Item Description Structure
Catalog 8825 CAS 148347-88-0
Product Name (-)-Bis[1-{(1'S,2'S,5'R)-2'-i-propyl-5'-methylcyclohexyl}indenyl]zirconium(IV) dichloride
Other Name Dichlorobis[(1,2,3,3a,7a-)-1-[(1S,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl]-1H-inden-1-yl]-zirconium
Dichlorobis(1-neomenthylindenyl)-zirconium
Purity 97% ee NA
Molecular Formula C38H50Cl2Zr
Molecular Weight 668.93
Color and Form orange pwdr
Package 5g/10g and more Bulk Ordering Package
Solubility NA
Melting point >195 C (dec.)
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

Application

Prof. Ei-ich Negishis group has reported the Zirconium-Catalyzed Asymmetric Carboalumination of Alkenes (ZACA) reaction. The ZACA catalyst is a prototypical catalyst for asymmetric carbon-carbon bond formation, used for the efficient and selective synthesis of chiral organic compounds and natural products.
Catalyst for:
Carboalumination of alkenes
Asymmetric carboalumination
Intramolecular olefin coupling
Polymerization of propylene
1. Catalyst used for the enantioselective carboalumination of unactivated alkenes.
2. Catalyst used for the enantioselective synthesis of methyl-substituted alkanols and their
derivatives.
3. Reagent for the synthesis of reduced polypropionates via one pot Zr-catalyzed asymmetric
carboalumination Pd-catalyzed cross-coupling tandem process.
4. Catalyst used for the asymmetric carboalumination of internally hydroxylated terminal alkenes

1. L. V. Parfenova, et al., Tetrahedron Asymmetry 21, 299-310, (2010)
2. Efficient and selective synthesis of (S,R,R,S,R,S)-4,6,8,10,16,18-hexamethyl-docosane via Zr-catalyzed asymmetric carboalumination of alkenes (ZACA reaction). G. Zhu, et al., Org. Lett. 10, 1099-1101, (2008)
3. S. Thiele and G. Erker, Chem. Ber. 130, 201-207, (1997)
4. M. Knickmeier, et al., J. Am. Chem. Soc. 118, 9623-9630, (1996)
5. Total synthesis of (+)-scyphostatin featuring an enantioselective and highly efficient route to the side-chain via Zr-catalyzed asymmetric carboalumination of alkenes (ZACA). Emmanuel, P.; Negishi, E. et al. Chem. Commun. 46, 2200, (2010)
6. 1,4-Pentenyne as a five-carbon synthon for efficient and selective syntheses of natural products containing 2,4-dimethyl-1-penten-1,5-ylidene and related moieties by means of Zr-catalyzed carboalumination of alkynes and alkenes. Zhu, G.; Negishi, E. Chem. Eur. J. 14, 311, (2008)
7. Huang, Z.; Negishi, E. et al. Adv. Synth. Catal. 349, 539, (2007)
8. Fully reagent-controlled asymmetric synthesis of (-)-spongidepsin via the Zr-catalyzed asymmetric carboalumination of alkenes (ZACA reaction). Zhu, G.; Negishi, E. Org. Lett. 9, 2771, (2007)
9. Catalytic, efficient, and syn-selective construction of deoxypolypropionates and other chiral compounds via Zr-catalyzed asymmetric carboalumination of allyl alcohol. Liang, B.; Negishi, E. et al. J. Am. Chem. Soc. 128, 2770, (2006)
References:
1. Pure Appl. Chem., 2002, 74(1), 151.
2. Angew. Chem. Int. Ed., 2002, 41, 2141.
3. J. Am. Chem. Soc., 2005, 127, 2838.
4. Org. Lett., 2007, 9, 2771.

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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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