Article Dans Une Revue Journal of Organic Chemistry Année : 2007

Suzuki Cross-Coupling on Enantiomerically Pure Epoxides: Efficient Synthesis of Diverse, Modular Amino Alcohols from Single Enantiopure Precursors

Résumé

Suzuki arylation of enantiopure (4-bromophenyl)- or (3,5-dibromophenyl)glycidyl ethers has been achieved in toluene under Buchwald conditions [ArB(OH)2 (1.1 equiv), Cs2CO3 (2 equiv), Pd2(dba)3·C6H6 (1 mol %), S-Phos (4 mol %), toluene, 100 C] allowing for the formation of modular arylglycidyl ethers not directly available in enantiopure form by epoxidation routes. These bulky ethers, when submitted to regioselective and stereospecific ring opening with ammonia [aq NH3, LiClO4 (1 equiv), THF, microwave irradiation (80 W), 125 C] in a sealed tube, provide access to novel enantiopure -amino alcohols which, in turn, provide an easy access to structurally complex C2 symmetrical bisoxazolines.

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Dates et versions

hal-00180035 , version 1 (17-10-2007)

Identifiants

Citer

Xavier Cattoën, Miquel A. Pericàs. Suzuki Cross-Coupling on Enantiomerically Pure Epoxides: Efficient Synthesis of Diverse, Modular Amino Alcohols from Single Enantiopure Precursors. Journal of Organic Chemistry, 2007, 72 (9), pp.3253-3258. ⟨10.1021/jo062612t⟩. ⟨hal-00180035⟩
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