Heterocycles

Reactivity of (R)-4-phenyloxazolidin-2-thione chiral auxiliary: from deprotection to heterocyclic interconversion

JC Monbaliu, B Tinant, J Marchand-Brynaert

文献索引：Monbaliu, Jean-Christophe; Tinant, Bernard; Marchand-Brynaert, Jacqueline Heterocycles, 2008 ,  vol. 75,  # 10  p. 2459 - 2475

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被引用次数: 2

摘要

Using (R)-3-beilzyl-4-phenyloxazolidin-2-thione (2) as model compound, a sequence of reactions has been established that allows the chiral auxiliary deprotection to furnish a primary amine. Treatment of 2 with ethyl triflate (3b) followed by ring opening with RbI (4b) and HI elimination with DBU, in a one pot process, gave S-ethyl-N-benzyl-N-1- phenylvinylcarbamothioate (5, 95% yield) which acid hydrolysis (9) and saponification ...