郭其祥课题组科研成果|手性醛催化平台助力非天然氨基酸与手性胺高效合成
2026-05-20 · 推荐产品 · 百灵威授权转载
手性胺和非天然氨基酸的合成，长期面临保护/脱保护步骤繁琐、立体选择性控制困难等问题。
西南大学郭其祥教授团队基于亚胺活化机制的手性醛催化新策略，开发系列轴手性联萘醛催化剂，被国际同行命名为 Guo's BINOLs，开辟无需氨基保护的氨基酸直接不对称 α- 官能化新路径——为手性胺和非天然氨基酸的合成提供了全新工具。
核心技术优势
优势一：无需保护基，步骤经济
传统方法需要对氨基进行保护/脱保护，步骤冗长。本技术利用手性醛与伯胺的可逆缩合，直接活化α-C-H键，简化了合成路线。
优势二：立体选择性优异
通过手性醛催化剂的手性控制模型，可实现高效的不对称诱导。第二代手性醛催化剂[1]底物范围宽、立体选择性高，并入选中国化学会《2018-2019化学学科发展报告》。
优势三：联合催化，拓展反应类型
突破传统手性醛催化需要高活性试剂的局限，将手性醛与过渡金属联合催化[2]，实现氨基酸酯与烯丙醇酯的不对称α-烯丙基化，成功构建α-季碳手性中心。
优势四：催化剂家族完整，适用性广
从第一代3-甲酰基联萘系列[3]到第二代2-甲酰基联萘系列，已发展出数十个手性醛催化剂，可匹配不同底物和反应需求。
应用场景
使用轴手性联萘醛催化剂，可自主合成：
一、手性胺
手性胺是众多小分子药物生产线上不可或缺的“通用零件”。可用于合成β-受体阻滞剂（如美托洛尔）、抗生素、抗病毒药物（如HIV蛋白酶抑制剂）等医药中间体，也可用于手性农药和除草剂的合成。
二、非天然手性氨基酸
非天然手性氨基酸是新一代生物大分子药物（尤其是多肽药物）实现“功能升级”的关键“智能零件”。可用于多肽药物（如司美鲁肽）、ADC药物、蛋白质工程（遗传密码扩展技术）以及新型生物材料的开发。
百灵威可稳定供应联萘手性醛催化剂（Guo's BINOLs），助力手性胺与非天然氨基酸的高效不对称合成研究。3-甲酰基联萘系列
| 品名 | CAS | 货号 |
|---|---|---|
| 2,2′-Dihydroxy-[1,1′-binaphthalene]-3-carbaldehyde, 98% (S)-2,2'-二羟基-[1,1'-联萘]-3-醛 | 345659-34-9 | 9222125 |
| (1R)-2-Hydroxy-2′-methyl-[1,1′-binaphthalene]-3-carbaldehyde-, 98% (R)-2-羟基-2'-甲基-[1,1'-联萘]-3-甲醛 | 158010-19-6 | 9718726 |
| (1R)-2-Hydroxy-2′-methoxy[1,1′-binaphthalene]-3-carboxaldehyde, 98% (1R)-2 - 羟基 - 2’- 甲氧基 -[1,1'- 联萘]-3 - 甲醛 | 873439-62-4 | 9718727 |
| (1R)2-Hydroxy-[1,1′-binaphthalene]-3-carbaldehyde , 98% (1R)-2 - 羟基 -[1,1’- 联萘]-3 - 甲醛 | 337379-89-2 | 9718728 |
| (1R)-3′-(3,5-Dimethoxyphenyl)-2,2′-dihydroxy-[1,1′-binaphthalene]-3-carboxaldehyde, 98% (1R)-3'-(3,5 - 二甲氧基苯基)-2,2'- 二羟基 -[1,1'- 联萘]-3 - 甲醛 | 2240192-34-9 | 9718729 |
| (1R)-3′-(3,5-Difluorophenyl)-2,2′-dihydroxy[1,1′-binaphthalene]-3-carboxaldehyde, 98% (1R)-3'-(3,5 - 二氟苯基)-2,2'- 二羟基 -[1,1'- 联萘]-3 - 甲醛 | 2240192-30-5 | 9718730 |
| (1R)-2,2′-Dihydroxy-3′-[4-(trifluoromethyl)phenyl][1,1′-binaphthalene]-3-carboxaldehyde , 98% (1R)-2,2'- 二羟基 - 3'-[4-(三氟甲基) 苯基]-[1,1' - 联萘]-3 - 甲醛 | 2240192-27-0 | 9718731 |
| (1R)-3′-[3,5-Bis(trifluoromethyl)phenyl]-2,2′-dihydroxy[1,1′-binaphthalene]-3-carboxaldehyde, 98% (1R)-3'-[3,5 - 双 (三氟甲基) 苯基]-2,2'- 二羟基 -[1,1'- 联萘]-3 - 甲醛 | 2240192-31-6 | 9718732 |
| (1R)-3′-(3,5-Dimethylphenyl)-2,2′-dihydroxy[1,1′-binaphthalene]-3-carboxaldehyde , 98% (1R)-3'-(3,5-二甲基苯基)-2,2'-二羟基[1,1'-联萘]-3-甲醛 | 2240192-33-8 | 9718733 |
| (1R)-3′-(4-Chlorophenyl)-2,2′-dihydroxy[1,1′-binaphthalene]-3-carboxaldehyde , 98% (1R)-3'-(4-氯苯基)-2,2'-二羟基[1,1'-联萘]-3-甲醛 | 2240192-26-9 | 9718734 |
| (1R)-3′-(4-Fluorophenyl)-2,2′-dihydroxy[1,1′-binaphthalene]-3-carboxaldehyde , 98% (1R)-3'-(4-氟苯基)-2,2'-二羟基[1,1'-联萘]-3-甲醛 | 2240192-25-8 | 9718735 |
| (1R)-2,2′-Dihydroxy-3′-(4-methoxyphenyl)[1,1′-binaphthalene]-3-carboxaldehyde , 98% (1R)-2,2'-二羟基-3'-(4-甲氧基苯基)[1,1'-联萘]-3-甲醛 | 2240192-28-1 | 9718736 |
| (1R)-2,2'-Dihydroxy[1,1':3',2''-ternaphthalene]-3-carboxaldehyde, 98% (1R)-2,2'-二羟基[1,1':3',2''-三联萘]-3-甲醛 | 2240192-36-1 | 9718737 |
| (1R)-2,2'-Dihydroxy-3'-(9-phenanthrenyl)[1,1'-binaphthalene]-3-carboxaldehyde, 98% (1R)-2,2'-二羟基-3'-(9-菲基)[1,1'-联萘]-3-甲醛 | 2240192-38-3 | 9718738 |
| (1R)-2,2'-Dihydroxy-3'-phenyl[1,1'-binaphthalene]-3-carboxaldehyde, 98% (1R)-2,2'-二羟基-3'-苯基[1,1'-联萘]-3-甲醛 | 2240192-24-7 | 9718739 |
| (1R)-2,2'-Dihydroxy-3'-methyl[1,1'-binaphthalene]-3-carboxaldehyde, 98% (1R)-2,2'-二羟基-3'-甲基[1,1'-联萘]-3-醛 | 2240192-23-6 | 9718740 |
| (1R)-2,2'-Dihydroxy-3'-iodo[1,1'-binaphthalene]-3-carboxaldehyde, 98% (1R)-2,2'-二羟基-3'-碘[1,1'-联萘]-3-醛 | 2240192-22-5 | 9718741 |
| (1R)-2,2'-Dihydroxy-3'-bromo-[1,1'-binaphthalene]-3-carbaldehyde, 98% (1R)-2,2'-二羟基-3'-溴[1,1'-联萘]-3-醛 | 497157-26-3 | 9718742 |
| (1R)-2,2'-Dihydroxy-3'-chloro-[1,1'-binaphthalene]-3-carbaldehyde, 98% (1R)-2,2'-二羟基-3'-氯[1,1'-联萘]-3-醛 | 2416767-07-0 | 9718743 |
| (1R)-2,2'-Dihydroxy-3'-(trimethylsilyl)[1,1'-binaphthalene]-3-carboxaldehyde, 98% (1R)-2,2'-二羟基-3'-(三甲基硅烷)[1,1'-二萘]-3-醛 | 2304799-62-8 | 9718744 |
| (1R)-2,2'-Dihydroxy-3'-formyl-[1,1'-binaphthalene]-3-carboxaldehyde, 98% (1R)-2,2'-二羟基-3'-甲腈[1,1'-联萘]-3-醛 | 2416767-09-2 | 9718745 |
| (1S)-[1,1'-Binaphthalene]-3-carboxaldehyde,4',6,6'-tribromo-2,2'-dihydroxy, 98% (1S)-4',6,6'-三溴-2,2'-二羟基-[1,1'-联萘]-3-甲醛 | 2640004-39-1 | 9718746 |
| (1R)-2,2'-Dihydroxy-3'-(9-Anthracenyl)-[1,1'-binaphthalene]-3-carbaldehyde, 98% (1R)-2,2'-二羟基-3'-(9-蒽基)[1,1'-联萘]-3-醛 | 2240192-37-2 | 9718747 |
| (1R)-2,2'-Dihydroxy-[1,1':3',1''-ternaphthalene]-3-carbaldehyde, 98% (1R)-2,2'-二羟基[1,1':3',1''-萘]-3-甲醛 | 2240192-35-0 | 9718748 |
| (1R)-2'-[3,5-Bis(trifluoromethyl)phenyl]-2-hydroxy[1,1'-binaphthalene]-3-carboxaldehyde, 98% (1R)-2'-[3,5-双(三氟甲基)苯基]-2-羟基[1,1'-联萘]-3-甲醛 | 1384934-36-4 | 9718751 |
2-甲酰基联萘系列
| 品名 | CAS | 货号 |
|---|---|---|
| (1S)-4-Bromo-3-hydroxy[1,1'-binaphthalene]-2-carboxaldehyde, 98% (1S)-4-溴-3-羟基-1,1'-联萘-2-甲醛 | 2416767-18-3 | 9718749 |
| (1S)-2'-[3,5-Bis(1,1-dimethylethyl)phenyl]-4-bromo-3-hydroxy[1,1'-binaphthalene]-2-carboxaldehyde, 98% (1S)-2'-(3,5-二叔丁基苯基)-4-溴-3-羟基-[1,1'-联萘]-2-甲醛 | 2416767-20-7 | 9718750 |
| (1S)-4-Bromo-2'-[4-(1,1-dimethylethyl)phenyl]-3-hydroxy[1,1'-binaphthalene]-2-carboxaldehyde, 98% (1S)-4-溴-2'-(4-叔丁基苯基)-3-羟基[1,1'-联萘]-2-甲醛 | 2240192-20-3 | 9718752 |
| (1S)-4-Bromo-3-hydroxy[1,1':2',2''-ternaphthalene]-2-carboxaldehyde, 98% (1S)-4-溴-3-羟基[1,1':2',2''-三联萘]-2-甲醛 | 2240192-18-9 | 9718753 |
| (1S)-3-Hydroxy-4-iodo-2'-phenyl[1,1'-binaphthalene]-2-carboxaldehyde, 98% (1S)-3-羟基-4-碘-2'-苯基[1,1'-联萘]-2-甲醛 | 2240192-17-8 | 9718754 |
| (1S)-2'-(Biphenyl-4-yl)-4-bromo-3-hydroxy[1,1'-binaphthalene]-2-carboxaldehyde, 98% (1S)-2'-(联苯-4-基)-4-溴-3-羟基[1,1'-联萘]-2-甲醛 | 2416767-19-4 | 9718755 |
| (1S)-4-Bromo-3-hydroxy-2'-phenyl[1,1'-binaphthalene]-2-carboxaldehyde, 98% (1S)-4-溴-3-羟基-2'-苯基[1,1'-联萘]-2-甲醛 | 2240192-16-7 | 9718756 |
| (1S)-3-Hydroxy-2'-phenyl[1,1'-binaphthalene]-2-carboxaldehyde, 98% (1S)-3-羟基-2'-苯基[1,1'-联萘]-2-甲醛 | 2240191-96-0 | 9718757 |
过度金属催化剂
| 品名 | CAS | 货号 |
|---|---|---|
| Allylpalladium(II) chloride dimer, 98% 氯化烯丙基钯(II)二聚物 | 12012-95-2 | 982398 |
| Tetrakis(triphenylphosphine)palladium(0), 99% 四(三苯基膦)钯(0) | 14221-01-3 | 182482 |
| Palladium(II) acetate, 47.5% Pd 醋酸钯(II) | 3375-31-3 | 234582 |
| Tris(dibenzylideneacetone)dipalladium(0), 20% Pd 三(二亚苄基丙酮)二钯(0) | 51364-51-3 | 960139 |
| [1,2-Bis(diphenylphosphino)ethane]dichloronickel(II), 99% [1,2-双(二苯基膦)乙烷]二氯化镍(II) | 14647-23-5 | 102993 |
膦配体
| 品名 | CAS | 货号 |
|---|---|---|
| 1,3-Bis(diphenylphosphino)propane, 98% 1,3-双(二苯基膦)丙烷 | 6737-42-4 | 161283 |
| 1,2-Bis(diphenylphosphino)ethane, 97%, for synthesis 1,2-双(二苯基膦)乙烷 | 1663-45-2 | 148746 |
| 1,1'-Bis(diphenylphosphino)ferrocene, 98% 1,1'-双(二苯基膦)二茂铁 | 12150-46-8 | 231095 |
| Triphenylphosphine, 99% 三苯基膦 | 603-35-0 | 110246 危化品 |
| 1,4-Bis(diphenylphosphino)butane, 98% 1,4-双(二苯基膦)丁烷 | 7688-25-7 | 145240 |
路易斯酸
| 品名 | CAS | 货号 |
|---|---|---|
| Zinc chloride, 98%, AR 氯化锌 | 7646-85-7 | 991518 危化品 |
| Zinc trifluoromethanesulfonate, 97.5% 三氟甲磺酸锌 | 54010-75-2 | 147935 |
| Zinc bromide, 98% 溴化锌 | 7699-45-8 | 942812 |
| Zinc fluoride, 99% 氟化锌 | 7783-49-5 | 446487 危化品 |
| Zinc acetate, 99.99% 乙酸锌 | 557-34-6 | 928202 |
| Magnesium trifluoromethanesulfonate, 98% 三氟甲烷磺酸镁 | 60871-83-2 | 152796 |
碱
| 品名 | CAS | 货号 |
|---|---|---|
| Cesium carbonate, 99% 碳酸铯 | 534-17-8 | 129355 |
| Potassium carbonate, 99% 碳酸钾 | 584-08-7 | 212583 |
| Sodium bicarbonate, 99.5%, for analysis 碳酸氢钠 | 144-55-8 | 907280 |
| 2,6-Lutidine, 99% 2,6-二甲基吡啶 | 108-48-5 | 291976 危化品 |
| 1,8-Diazabicyclo[5.4.0]undec-7-ene, 98% 1,8-二氮杂双环[5.4.0]十一碳-7-烯 | 6674-22-2 | 292269 |
| 1,5,7-Triazabicyclo[4.4.0]dec-5-ene, 98% 1,5,7-三氮杂二环[4.4.0]癸-5-烯 | 5807-14-7 | 478441 |
| 1,5-Diazabicyclo[4.3.0]non-5-ene, 99% 1,5-二氮杂双环[4.3.0]壬-5-烯 | 3001-72-7 | 929402 |
| 1,1,3,3-Tetramethylguanidine, 98% 1,1,3,3-四甲基胍 | 80-70-6 | 940257新 |
溶剂
| 品名 | CAS | 货号 |
|---|---|---|
| Dichloromethane, 99.9%, SuperDry, stabilized with amylene, water≤30 ppm, J&KSeal 二氯甲烷 | 75-09-2 | 961203促 危化品 |
| Tetrahydrofuran, 99.5%, SuperDry, with molecular sieves, stabilized with 250 ppm BHT, Water≤50 ppm, J&KSeal 四氢呋喃 | 109-99-9 | 974643促 危化品 |
| 1,2-Dichloroethane, 99.5%, SuperDry, water≤30 ppm, J&Kseal 1,2-二氯乙烷 | 107-06-2 | 991050促 危化品 |
参考文献
- Wei Wen, Lei Chen, Ming-Jing Luo, Yan Zhang, Ying-Chun Chen, Qin Ouyang, Qi-Xiang Guo. Chiral Aldehyde Catalysis for the Catalytic Asymmetric Activation of Glycine Esters. J. Am. Chem. Soc. 2018, 140, 30, 9774–9780.
- Lei Chen, Ming-Jing Luo, Fang Zhu, Wei Wen, Qi-Xiang Guo. Combining Chiral Aldehyde Catalysis and Transition-Metal Catalysis for Enantioselective α-Allylic Alkylation of Amino Acid Esters. J. Am. Chem. Soc. 2019, 141, 13, 5159–5163.
- B Xu, LL Shi, YZ Zhang, ZJ Wu, LN Fu, CQ Luo, LX Zhang, YG Peng, QX Guo. Catalytic asymmetric direct α-alkylation of amino esters by aldehydes via imine activation. Chem. Sci. 2014, 5, 1988-1991.
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