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Allylations

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Recent Literature

A simple method for the chemo- and regioselective, direct catalytic allylic alkylation of aldehydes and cyclic ketones has been developed. The combination of palladium and enamine catalysis furnished α-allylic alkylated aldehydes and cyclic ketones in high yields.
I. Ibrahem, A. Córdova, Angew. Chem. Int. Ed., 2006, 45, 1952-1956.

I. Ibrahem, A. Córdova, Angew. Chem. Int. Ed., 2006, 45, 1952-1956.

A highly enantioselective Pd/chiral acid-catalyzed α-allylation of α-branched aldehydes with an allyl amine as the allylating species creates all-carbon quaternary stereogenic centers in high yields and enantioselectivities.
S. Mukherjee, B. List, J. Am. Chem. Soc., 2007, 129, 11336-11337.

A combination of [Ir(COD)Cl]₂and a phosphoramidite ligand is an efficient catalytic system for a highly regio- and enantioselective decarboxylative alkylation of γ-substituted allyl β-ketocarboxylates, affording branched products with a regioselectivity of up to 99:1 and 96% ee.
H. He, X.-J. Zheng, Y. Li, L.-X. Dai, S.-L. You, Org. Lett., 2007, 9, 4339-4341.

Catalytic enantioselective examples of the Tsuji allylation using enol carbonates and enol silanes gave products possessing a quaternary stereogenic center, which are useful building blocks for synthetic chemistry.
D. C. Behenna, B. M. Stoltz, J. Am. Chem. Soc., 2004, 126, 15044-15045.

D. C. Behenna, B. M. Stotz, J. Am. Chem. Soc., 2004, 126, 15044-15045.

A catalytic enantioconvergent synthesis of quaternary stereocenters from racemates with quaternary stereocenters has been developed. A chiral Pd catalyst is involved in both the stereoablative (C-C bond-breaking) and stereoselective (C-C bond-forming) steps.
J. T. Mohr, D. C. Behenna, A. M. Harned, B. M. Stoltz, Angew. Chem. Int. Ed., 2005, 44, 6924-6927.

In a new, efficient, catalytic asymmetric protocol for the synthesis of α-tertiary hydroxyaldehydes from readily available α-halo or α-hydroxy ketones or enol silyl ethers, the chiral ligand controls the regioselectivity as well as the enantioselectivity.
B. M. Trost, J. Xu, M. Reichle, J. Am. Chem. Soc., 2007, 129, 282-283.

Stereodefined enol derivatives of aldehydes are prepared from terminal alkynes through Cp₂ZrCl₂-catalyzed methylalumination and subsequent oxygenation with peroxyzinc species and electrophilic trapping with carboxylic anydrides. The tandem carbometalation/oxygenation tolerates free and protected alcohols, heterocycles, olefins, and nitriles.
J. R. DeBergh, K. M. Spivey, J. M. Ready, J. Am. Chem. Soc., 2008, 130, 7828-7829.