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首页> 外文期刊>RSC Advances >Stereoselective synthesis and application of isopulegol-based bi- and trifunctional chiral compounds
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Stereoselective synthesis and application of isopulegol-based bi- and trifunctional chiral compounds

机译：基于异氟醚的双孔和三官能手性化合物的立体选择性合成与应用

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A new family of isopulegol-based bi- and trifunctional chiral ligands was developed from commercially available (?)-isopulegol. Nucleophilic addition of primary amines towards (+)-α-methylene-γ-butyrolactone was accomplished, followed by reduction of the obtained β-aminolactones to provide aminodiols in highly stereoselective reactions. Epoxidation of (?)-isopulegol and subsequent oxirane ring opening with primary amines resulted in N -substituted aminodiols. The regioselective ring closure of these aminodiols with formaldehyde was also investigated. Benzylation of isopulegol furnished O -benzyl-protected isopulegol, which was transformed into aminoalcohols via epoxidation and ring opening of the corresponding epoxides. First benzyl-protected isopulegol was subjected to hydroxylation and epoxidation, then aminolysis of the served oxiranes delivered aminodiols. On the other hand, (?)-isopulegol was oxidised to diol, which was again converted into both dibenzyl- and monobenzyl-protected diol derivatives. The products were transformed into aminoalcohols and aminodiols, respectively, by aminolysis of their epoxides. The ring opening of epoxides, derived from diols with primary amines was also performed producing aminotriols. Dihydroxylation of (?)-isopulegol or derivatives with OsO _(4) /NMO gave isopulegol-based di-, tri- and tetraols. The antimicrobial activity and antioxidant property, measuring DPPH˙ free radical scavenging activity of aminodiol and aminotriol derivatives as well as di-, tri- and tetraols were also explored. In addition, structure–activity relationships were examined from the aspects of substituent effects and stereochemistry on the aminodiol and aminotriol systems.
机译：从市售（α） - 异浮子醇中，开发了一种新的基于异孔和三官能的手性配体的基于异孔和三官能手性配体。完成初级胺的亲核加入致（+） - α-甲基-γ-丁内酯，然后减少所得β-氨基氨基，以在高度立体化反应中提供氨基二醇。 （α） - 异氟醚和随后的氧乙烷环开口与伯胺的环氧化导致N-取代的氨基醇。还研究了这些氨基二醇与甲醛的区域选择性环闭合。异孔的苄基化提供O-苄基保护的异氟醚，通过环氧化和相应环氧化物的环开口转化为氨基醇。首先对苄基保护的异氟醚进行羟基化和环氧化，然后氨基溶于氨基二醇递送的氧化氧化醇。另一方面，（？） - 异氟醚被氧化成二醇，再次转化成二苄基和单苄基 - 保护的二醇衍生物。通过氨基氧化物分析产物分别转化为氨基醇和氨基二醇。还在产生氨基丙醇的二醇中衍生自二醇的环氧化物的开环。 （α） - 异氟醚或衍生物的二羟基化或含有OSO _（4）/ NMO的衍生物，得到了基于异硫醇的二 - ，三 - 和四元。还探讨了抗微生物活性和抗氧化性能，测量氨基二醇和氨基二醇衍生物的自由基清除活性以及二 - ，三元和四元的抗氧化剂。此外，从氨基二醇和氨基醇系统的取代效应和立体化学方面检查了结构活性关系。

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