1027299-78-0Relevant academic research and scientific papers
Suzuki cross-coupling on enantiomerically pure epoxides: Efficient synthesis of diverse, modular amino alcohols from single enantiopure precursors
Cattoen, Xavier,Pericas, Miquel A.
, p. 3253 - 3258 (2008/02/03)
(Chemical Equation Presented) 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), Cs 2CO3 (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 NH 3, LiClO4 (1 equiv), THF, microwave irradiation (80 W), 125°C] in a sealed tube, provide access to novel enantiopure β-amino alcohols which, in turn, provide an easy access to structurally complex C 2 symmetrical bisoxazolines.
