Mechanism and Extensibility of the Reaction

Alkylcerium reagents add to the multiple bonds of allyl and propargyl alcohols in good yields and under mild conditions. The double bond can be reduced with lithium aluminum hydride in the presence of cerium trichloride. The regiochemistry of the attack depends on electronic factors.

[1]  Kak‐Shan Shia,et al.  Organocerium compounds in synthesis , 1999 .

[2]  A. Tagarelli,et al.  Reactivity of Organocerium Compounds with Allyl Alcohols. , 1998 .

[3]  E. Marcantoni,et al.  Synthesis of beta,gamma-unsaturated ketones via cerium-mediated addition of organolithiums to silylated enaminones , 1998 .

[4]  U. Groth,et al.  Ligand Effects in Diastereoselective Additions of Organocerium Reagents to Carbonyl Substrates , 1997 .

[5]  F. Nobili,et al.  Cerium (III) Chloride, a Novel Reagent for Nonaqueous Selective Conversion of Dioxolanes to Carbonyl Compounds , 1997 .

[6]  J. Edwards,et al.  Acyclic Stereoselection in the Ortho Ester Claisen Rearrangement. , 1997, The Journal of organic chemistry.

[7]  E. Marcantoni,et al.  A Stereoselective Synthesis of (E)‐α, β‐Unsaturated Ketones Involving the Reactions of Organocerium Reagents with Secondary β‐Enamino Ketones , 1996 .

[8]  E. Marcantoni,et al.  Cerium(III) Chloride Promoted Nucleophilic Addition of Organolithium Reagents to α‐Alkyl‐β‐Ketophosphine Oxides: A New Protocol for the Synthesis of Stereochemically Defined Trisubstituted Olefins , 1995 .

[9]  E. Marcantoni,et al.  Cerium(III) chloride mediated Michael addition of RMgX to nitroenes: A very efficient access to complex nitroalkanes , 1994 .

[10]  E. Marcantoni,et al.  Cerium chloride (III) promoted nucleophilic addition of organolithium reagents to α-diphenylphosphinoyl ketones. An efficient method for the synthesis of horner-wittig intermediates , 1994 .

[11]  G. Roos,et al.  Ephedrine‐Derived Imidazolidin‐2‐ones. Broad Utility Chiral Auxiliaries in Asymmetric Synthesis , 1993 .

[12]  J. Edwards,et al.  Organocerium Additions to Hydrazones: Effects of Reagent Stoichiometry on Efficiency and Selectivity , 1993 .

[13]  M. Reetz,et al.  Ligand effects in selective carbonyl addition reactions of organomanganese and cerium reagents , 1992 .

[14]  B. Grant,et al.  Regiocontrol in copper-catalyzed Grignard reactions with allylic substrates , 1990 .

[15]  T. Imamoto Carbonyl addition reactions promoted by cerium reagents , 1990 .

[16]  M. Schlosser,et al.  A stereocontrolled access to vicinal difluoroalkanes , 1988 .

[17]  H. L. Goering,et al.  Alkylation of allylic derivatives. 11. Copper(I)-catalyzed cross coupling of allylic carboxylates with Grignard reagents , 1986 .

[18]  C. Screttas,et al.  Synthesis of benzhydryl ethers by a carbon-carbon bond-forming reaction using benzhydryl 2-chloroethyl ether. A method for attaching a protected 2-hydroxyethyl group to a benzylic carbon , 1982 .

[19]  D. Abenhaim,et al.  The ate complexes of aluminium: Reactivity and stereoselectivity with respect to epoxides and carbonyl compounds. Catalytic activation by salts of transition metals , 1980 .

[20]  S. Murahashi,et al.  Stereoselective synthesis of alkenes and alkenyl sulfides from alkenyl halides using palladium and ruthenium catalysts , 1979 .

[21]  J. Eisch,et al.  Rearrangements of organometallic compounds. 15. Structural factors in the facile carbomagnesiation of isolated carbon-carbon double bonds , 1979 .

[22]  J. Crandall,et al.  Cis reduction of acetylenes by organocopper reagents , 1976 .