手性二苯基乙二醇衍生物的合成、结构表征及催化性能研究
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摘要
不对称催化是手性合成中极富前景的发展方向,其中新型手性催化剂是不对称催化研究的核心内容。本文以手性二醇为手性源,设计并合成了一系列含氮杂环的手性衍生物,研究了相关化合物的晶体结构和一些手性催化剂对二乙基锌与苯甲醛加成反应的不对称催化效果。主要工作如下：
1、通过Sharpless不对称双羟基化反应,合成了高纯度的(1R,2R)-1,2-二苯基乙二醇。以叔丁基二甲基氯硅烷(TBDCS)作为硅醚化试剂,对(1R,2R)-1,2-二苯基乙二醇进行单硅醚化保护,并与2-溴甲基吡啶溴酸盐、含甲氧基或N-吗啉取代的氰尿酰氯衍生物反应,经过(n-Bu)4NF脱保护后得到一系列含羟基的手性衍生物。
2、以(1R,2R)-1,2-二苯基乙二醇为手性源,通过与吡啶甲酸或溴甲基吡啶溴酸盐反应合成了含吡啶的酯类和醚类化合物。
3、以(1R,2R)-1,2-二苯基乙二醇为手性源,采用两种方法合成了(1R,2R)-2-甲氧基-1,2-二苯基乙醇,并将其与氰尿酰氯的单烷氧基或单氨基取代物反应,合成了含一个三嗪环的C2对称手性衍生物。将(1R,2R)-1,2-二苯基乙醇与氰尿酰氯双取代化合物反应合成了含两个三嗪环的C2对称手性衍生物。
4、研究了化合物(1R,2R)-1,2-二苯基乙二醇二(4-吡啶甲酸)酯、(1R,2R)-2-羟基-1,2-二苯基乙醇-(3-吡啶甲酸)酯和二(2-((1R,2R)-1,2-二苯基-2-羟基乙氧基)甲基))吡啶的晶体结构。
化合物(1R,2R)-1,2-二苯基乙二醇二(4-吡啶甲酸)酯的晶体结构属单斜晶系,空间群P21,晶胞参数a=11.925(10)A,b=5.826(5)A,c=17.787(15)A,α=γ=90°,β=105.629(10)°,每个晶胞单元中含有两个化合物的分子。化合物(1R,2R)-2-羟基-1,2-二苯基乙醇-(3-吡啶甲酸)酯的晶体结构属单斜晶系,空间群P21,晶胞参数a=8.939(2)A,b=5.8128(14)A,c=16.191(4)A,a=γ=90°,p=100.303(3)°,每个晶胞单元中含有两个化合物的分子。化合物二(2-((1R,2R)-1,2-二苯基-2-羟基乙氧基)甲基))吡啶的晶体结构属于正交晶系,空间群P212121,晶胞参数a=5.4370(11)A,b=19.911(4)A,c=26.962(6)A,α=γ=β=90°,每个晶胞单元中有四个化合物分子。这些晶体的晶胞中都存在O—H...N氢键和C—H...O氢键,这些氢键作用的存在有利于晶胞的堆积和晶体的形成。
5、将设计、合成的含吡啶或三嗪环的六种(1R,2R)-1,2-二苯基乙二醇衍生物用于二乙基锌对苯甲醛加成反应的不对称催化中,初步研究表明,(1R,2R)-1,2-二苯基-乙二醇吡啶衍生物催化的立体选择性明显高于三嗪环衍生物催化剂,催化剂的立体选择性与其结构中手性中心上的羟基有关。
(1R,2R)-1,2-二苯基-乙二醇的醚键衍生物比酯基衍生物具有更好的光学催化活性。(1R,2R)-2-(2-吡啶甲氧基)-1,2-二苯基乙醇在催化反应中取得了78%的收率和56%ee的对映选择性。
Asymmetric catalystic reaction has recently been the subject of intense research in chiral syntheses where novel chiral catalysts are the core of the construction. Using (R,R)-hydrobenzoin as chiron, a series of chiral derivatives of nitrogen-containing heterocycles were synthesized.
The crystal structures of relative compounds and catalytic effects of some chiral derivatives on the enantioselective addition of diethylzinc to benzaldehyde have been studied.
1. The (R,R)-hydrobenzoin with high enantio-purity was prepared by Sharpless Asymmetric Dihydroxylation. The chiral derivatives containing hydroxyl group were synthesized from the reaction of 2-(Bromomethyl)pyridine hydrobromide, methoxy or N-morpholino derivatives of cyanuric chloride and the mono silicon etherification product of (R,R)-hydrobenzoin, followed by deprotection in the presence of (n-Bu)4NF.
2. Using (R,R)-hydrobenzoin as chiron, esters and ethers containing pyridine were synthesized by the reaction with pyridine acid or 2-(Bromomethyl)pyridine hydrobromide.
3. Using (R,R)-hydrobenzoin as raw material, two methods were studied to synthesize (1R,2R)-2-methoxy-1,2-bibenphenylethanol. The C2-symmetric chiral derivatives with one s-triazine ring were synthesized from (1R,2R)-2-methoxy-1,2-bibenphenylethanol and the derivatives of cyanuric chloride which were mono-substituted by alkoxy or amino group. The C2-symmetric chiral derivatives with double s-triazine rings were synthesized from (R,R)-hydrobenzoin and the derivatives of cyanuric chloride which were bi-substituted by methoxy or N-morpholino.
4. The crystal structures of (1R,2R)-1,2-diphenyl-1,2-diethyl isonicotinate (1R,2R)-2-hydroxy-1,2-diphenylethyl nicotinate and di(2-((1R,2R)-1,2-diphenylethyl-2-hydroxyethoxy)methy)) pyridine have been studied. The crystal of (1R,2R)-1,2-diphenyl-1,2-diethyl isonicotinate is monoclinic with space group P21,α= 11.925(10) A,b= 5.826(5) A, c= 17.787(15) A,α=γ= 90°,β= 105.629(10)°.It can be seen that two molecules exist in one unit cell. The crystal of (1R,2R)-2-hydroxy-1,2-diphenylethyl nicotinate is monoclinic with space group P21, a= 8.939(2) A, b= 5.8128(14) A, c 16.191(4) A,α=γ= 90°,β= 100.303(3)°. It can be seen that two molecules exist in one unit cell. The crystal of di(2-((1R,2R)-1,2-diphenylethyl-2- hydroxyethoxy)methy)) pyridine is Orthorhombic with space group P212121, a= 5.4370(11)A, b= 19.911(4)A, c= 26.962(6) A,α=γ=β= 90°. It can be seen that four molecules exist in one unit cell. The three crystal structures are stabilized by O-H...N or C-H...O hydrogen bond.
5. Six derivatives containing pyridine or triazine were studied as catalysts for the enantioselective addition of diethylzinc to benzaldehyde. The preliminary studies indicated that the enantioselectivity of pyridine-containing derivatives of (R,R)-hydrobenzoin is higher than that of triazine-containing derivatives. The results showed that stereoselectivity of catalysts is related to hydroxyl group attached to chiral carbon.
Ether derivatives were proved to be the better catalysts than the ester ones with regard to enantioselectivity. (1R,2R)-2-(2-pyridinemethoxy)-1,2-diphenylethanol yields in 78% and the enantioselectivity is 56%ee.
1、通过Sharpless不对称双羟基化反应,合成了高纯度的(1R,2R)-1,2-二苯基乙二醇。以叔丁基二甲基氯硅烷(TBDCS)作为硅醚化试剂,对(1R,2R)-1,2-二苯基乙二醇进行单硅醚化保护,并与2-溴甲基吡啶溴酸盐、含甲氧基或N-吗啉取代的氰尿酰氯衍生物反应,经过(n-Bu)4NF脱保护后得到一系列含羟基的手性衍生物。
2、以(1R,2R)-1,2-二苯基乙二醇为手性源,通过与吡啶甲酸或溴甲基吡啶溴酸盐反应合成了含吡啶的酯类和醚类化合物。
3、以(1R,2R)-1,2-二苯基乙二醇为手性源,采用两种方法合成了(1R,2R)-2-甲氧基-1,2-二苯基乙醇,并将其与氰尿酰氯的单烷氧基或单氨基取代物反应,合成了含一个三嗪环的C2对称手性衍生物。将(1R,2R)-1,2-二苯基乙醇与氰尿酰氯双取代化合物反应合成了含两个三嗪环的C2对称手性衍生物。
4、研究了化合物(1R,2R)-1,2-二苯基乙二醇二(4-吡啶甲酸)酯、(1R,2R)-2-羟基-1,2-二苯基乙醇-(3-吡啶甲酸)酯和二(2-((1R,2R)-1,2-二苯基-2-羟基乙氧基)甲基))吡啶的晶体结构。
化合物(1R,2R)-1,2-二苯基乙二醇二(4-吡啶甲酸)酯的晶体结构属单斜晶系,空间群P21,晶胞参数a=11.925(10)A,b=5.826(5)A,c=17.787(15)A,α=γ=90°,β=105.629(10)°,每个晶胞单元中含有两个化合物的分子。化合物(1R,2R)-2-羟基-1,2-二苯基乙醇-(3-吡啶甲酸)酯的晶体结构属单斜晶系,空间群P21,晶胞参数a=8.939(2)A,b=5.8128(14)A,c=16.191(4)A,a=γ=90°,p=100.303(3)°,每个晶胞单元中含有两个化合物的分子。化合物二(2-((1R,2R)-1,2-二苯基-2-羟基乙氧基)甲基))吡啶的晶体结构属于正交晶系,空间群P212121,晶胞参数a=5.4370(11)A,b=19.911(4)A,c=26.962(6)A,α=γ=β=90°,每个晶胞单元中有四个化合物分子。这些晶体的晶胞中都存在O—H...N氢键和C—H...O氢键,这些氢键作用的存在有利于晶胞的堆积和晶体的形成。
5、将设计、合成的含吡啶或三嗪环的六种(1R,2R)-1,2-二苯基乙二醇衍生物用于二乙基锌对苯甲醛加成反应的不对称催化中,初步研究表明,(1R,2R)-1,2-二苯基-乙二醇吡啶衍生物催化的立体选择性明显高于三嗪环衍生物催化剂,催化剂的立体选择性与其结构中手性中心上的羟基有关。
(1R,2R)-1,2-二苯基-乙二醇的醚键衍生物比酯基衍生物具有更好的光学催化活性。(1R,2R)-2-(2-吡啶甲氧基)-1,2-二苯基乙醇在催化反应中取得了78%的收率和56%ee的对映选择性。
Asymmetric catalystic reaction has recently been the subject of intense research in chiral syntheses where novel chiral catalysts are the core of the construction. Using (R,R)-hydrobenzoin as chiron, a series of chiral derivatives of nitrogen-containing heterocycles were synthesized.
The crystal structures of relative compounds and catalytic effects of some chiral derivatives on the enantioselective addition of diethylzinc to benzaldehyde have been studied.
1. The (R,R)-hydrobenzoin with high enantio-purity was prepared by Sharpless Asymmetric Dihydroxylation. The chiral derivatives containing hydroxyl group were synthesized from the reaction of 2-(Bromomethyl)pyridine hydrobromide, methoxy or N-morpholino derivatives of cyanuric chloride and the mono silicon etherification product of (R,R)-hydrobenzoin, followed by deprotection in the presence of (n-Bu)4NF.
2. Using (R,R)-hydrobenzoin as chiron, esters and ethers containing pyridine were synthesized by the reaction with pyridine acid or 2-(Bromomethyl)pyridine hydrobromide.
3. Using (R,R)-hydrobenzoin as raw material, two methods were studied to synthesize (1R,2R)-2-methoxy-1,2-bibenphenylethanol. The C2-symmetric chiral derivatives with one s-triazine ring were synthesized from (1R,2R)-2-methoxy-1,2-bibenphenylethanol and the derivatives of cyanuric chloride which were mono-substituted by alkoxy or amino group. The C2-symmetric chiral derivatives with double s-triazine rings were synthesized from (R,R)-hydrobenzoin and the derivatives of cyanuric chloride which were bi-substituted by methoxy or N-morpholino.
4. The crystal structures of (1R,2R)-1,2-diphenyl-1,2-diethyl isonicotinate (1R,2R)-2-hydroxy-1,2-diphenylethyl nicotinate and di(2-((1R,2R)-1,2-diphenylethyl-2-hydroxyethoxy)methy)) pyridine have been studied. The crystal of (1R,2R)-1,2-diphenyl-1,2-diethyl isonicotinate is monoclinic with space group P21,α= 11.925(10) A,b= 5.826(5) A, c= 17.787(15) A,α=γ= 90°,β= 105.629(10)°.It can be seen that two molecules exist in one unit cell. The crystal of (1R,2R)-2-hydroxy-1,2-diphenylethyl nicotinate is monoclinic with space group P21, a= 8.939(2) A, b= 5.8128(14) A, c 16.191(4) A,α=γ= 90°,β= 100.303(3)°. It can be seen that two molecules exist in one unit cell. The crystal of di(2-((1R,2R)-1,2-diphenylethyl-2- hydroxyethoxy)methy)) pyridine is Orthorhombic with space group P212121, a= 5.4370(11)A, b= 19.911(4)A, c= 26.962(6) A,α=γ=β= 90°. It can be seen that four molecules exist in one unit cell. The three crystal structures are stabilized by O-H...N or C-H...O hydrogen bond.
5. Six derivatives containing pyridine or triazine were studied as catalysts for the enantioselective addition of diethylzinc to benzaldehyde. The preliminary studies indicated that the enantioselectivity of pyridine-containing derivatives of (R,R)-hydrobenzoin is higher than that of triazine-containing derivatives. The results showed that stereoselectivity of catalysts is related to hydroxyl group attached to chiral carbon.
Ether derivatives were proved to be the better catalysts than the ester ones with regard to enantioselectivity. (1R,2R)-2-(2-pyridinemethoxy)-1,2-diphenylethanol yields in 78% and the enantioselectivity is 56%ee.
引文
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