可溶性聚合物支载手性噁唑烷-2-硫酮的合成

Synthesis of Non-cross-linked Polystyrene Supported(S)-4-[4′-((vinylbenzyl)oxy)benzyl]oxazolidine-2-thione

以N-Boc-L-酪氨酸乙酯为手性原料,经四步反应制备(S)-4-[4′-(对乙烯基苄氧基)苯基]噁唑烷-2-硫酮单体,以偶氮二异丁腈作为引发剂,与苯乙烯溶液聚合制备线性聚苯乙烯支载(S)-4-[4′-(对乙烯基苄氧基)苯基]噁唑烷-2-硫酮手性辅助试剂,总产率42%。该手性辅助试剂在CH2Cl2,THF,DMF等良溶剂具有很好的溶解性,进行均相不对称诱导反应,在甲醇等贫溶剂中不溶,反应完毕后,通过甲醇等溶剂沉淀洗涤,方便分离纯化和重复使用。

The(S)-4-[4′-((vinylbenzyl)oxy)benzyl]oxazolidine-2-thione monomer was synthesized by using N-tert-butoxycarbonyl-Boc-L-tyrosine ethyl ester as chiral material by four reactions.The non-crosslinked polystyrene supported(S)-4-[4′-((vinylbenzyl)oxy)benzyl] oxazolidine-2-thione was otained by the monomer copolymerized with styrene using AIBN as initiator in 42% overall yield.The obtained products has good solubility in CH2Cl2,THF,DMF and reacts as a homogeneous phase in solution. At the same time the obtained products which is easy recrystallized from MeOH has the advantages of easy seperation and purification.