Citation: Qing Fang CHENG, Xing You XU, Ming Yan WANG, Jun CHEN, Wei Xing MA, Xu Jie YANG. Enantioselective Pinacol Coupling of Aromatic Aldehydes Induced by Chiral Titanium Complexes[J]. Chinese Chemical Letters, ;2006, 17(7): 887-890. shu

Enantioselective Pinacol Coupling of Aromatic Aldehydes Induced by Chiral Titanium Complexes

1.
Department of Chemical Technology, Huaihai Institute of Technology, Lianyungang 222005;
2.
Materials Chemistry Laboratory, Nanjing University of Science and Technology, Nanjing 210094

Received Date: 10 January 2006

Asymmetric pinacol coupling of aromatic aldehydes with TiCl₄-Zn in the presence of enantiopure squaric acid amidoalcohols afforded 1, 2-diols in excellent yields with high dl-diastereoselectivities and enantioselectivities in the range of 46-89% ee. Some factors influencing dl-diastereoselectivity and enantioselectivity were discussed.
- Chiral squaric acid amidoalcohol,
- pinacol,
- asymmetric coupling,
- aromatic aldehyde
1. [1]
  Zhen Liu , Zhi-Yuan Ren , Chen Yang , Xiangyi Shao , Li Chen , Xin Li . Asymmetric alkenylation reaction of benzoxazinones with diarylethylenes catalyzed by B(C₆F₅)₃/chiral phosphoric acid. Chinese Chemical Letters, 2024, 35(5): 108939-. doi: 10.1016/j.cclet.2023.108939
2. [2]
  Jieshuai Xiao , Yuan Zheng , Yue Zhao , Zhuangzhi Shi , Minyan Wang . Asymmetric Nozaki-Hiyama-Kishi (NHK)-type reaction of isatins with aromatic iodides by cobalt catalysis. Chinese Chemical Letters, 2025, 36(5): 110243-. doi: 10.1016/j.cclet.2024.110243
3. [3]
  Wenyu Gao , Liming Zhang , Chuang Zhao , Lixiang Liu , Xingran Yang , Jinbo Zhao . Controlled semi-Pinacol rearrangement on a strained ring: Efficient access to multi-substituted cyclopropanes by group migration strategy. Chinese Chemical Letters, 2024, 35(9): 109447-. doi: 10.1016/j.cclet.2023.109447
4. [4]
  Haitao Liu , Youlin Deng , Dan Ling , Lingzhu Chen , Zhichao Jin . Asymmetric catalysis for the synthesis of planar chiral ferrocene derivatives. Chinese Chemical Letters, 2026, 37(3): 111793-. doi: 10.1016/j.cclet.2025.111793
5. [5]
  Long Jin , Jian Han , Dongmei Fang , Min Wang , Jian Liao . Pd-catalyzed asymmetric carbonyl alkynylation: Synthesis of axial chiral ynones. Chinese Chemical Letters, 2024, 35(6): 109212-. doi: 10.1016/j.cclet.2023.109212
6. [6]
  Yuanjiao Liu , Xiaoyang Zhao , Songyao Zhang , Yi Wang , Yutuo Zheng , Xinrui Miao , Wenli Deng . Site-selection and recognition of aromatic carboxylic acid in response to coronene and pyridine derivative. Chinese Chemical Letters, 2024, 35(8): 109404-. doi: 10.1016/j.cclet.2023.109404
7. [7]
  Feng Wu , Yuanjiu Xiao , Mengran Wei , Guoqiang Wang , Jian-Jun Feng . Lewis acid catalyzed enantioselective dearomative (3+2) cycloaddition of aromatic N-heterocycles with bicyclobutanes. Chinese Chemical Letters, 2026, 37(3): 111963-. doi: 10.1016/j.cclet.2025.111963
8. [8]
  Wei Peng , Yao Shen , Xiaolin Yu , Chenghang Zheng , Xiao Zhang , Jingkai Zhao , Jiexu Ye , Shihan Zhang , Xiang Gao . Asymmetric coupling of atop-type and hollow-type adsorbed *CO to boost electrocatalytic CO₂-to-C₂ conversion on high-index Cu₂O crystal planes. Chinese Chemical Letters, 2026, 37(1): 111187-. doi: 10.1016/j.cclet.2025.111187
9. [9]
  Pan Hu , Xiaofan Wu , Yi An , Xianjing Zheng , Liang Gao , Yuan Tao , Yajiao Zhang , Zedu Huang , Fener Chen . Batch and continuous-flow asymmetric synthesis of D-pantothenic acid precursor enabled by immobilized ketoreductase mutant. Chinese Chemical Letters, 2026, 37(2): 111945-. doi: 10.1016/j.cclet.2025.111945
10. [10]
  Ruixue Liu , Xiaobing Ding , Qiwei Lang , Gen-Qiang Chen , Xumu Zhang . Enantioselective and divergent construction of chiral amino alcohols and oxazolidin-2-ones via Ir-f-phamidol-catalyzed dynamic kinetic asymmetric hydrogenation. Chinese Chemical Letters, 2025, 36(3): 110037-. doi: 10.1016/j.cclet.2024.110037
11. [11]
  Xiuhua Wang , Jianrong Steve Zhou . A dicationic nickel complex-catalyzed asymmetric synthesis of chiral benzylic amines: Evolution from reductive amination to borrowing hydrogen reaction. Chinese Chemical Letters, 2026, 37(2): 111148-. doi: 10.1016/j.cclet.2025.111148
12. [12]
  Zhen-Qi Wang , Lin-Wen Wei , Zhao-Qing Wang , Yan-Jie Yang , Yu Zhao , Song Liu , Yuan Huang . Modular synthesis of polyfunctionalized axial-chiral 2-arylpyridines via cobalt-catalyzed asymmetric [2 + 2 + 2] cycloaddition of diynes and nitriles. Chinese Chemical Letters, 2026, 37(4): 111377-. doi: 10.1016/j.cclet.2025.111377
13. [13]
  Mengfan Zhang , Lingyan Liu , Peng Wei , Wei Feng , Tao Yi . A proximity tagging strategy utilizing an activated aldehyde group as the active site. Chinese Chemical Letters, 2025, 36(4): 110127-. doi: 10.1016/j.cclet.2024.110127
14. [14]
  Xiaojuan Lv , Yuting Dong , Hongliang Huang , Dariusz W. Szczepanik , Naoki Aratani , Takahisa Ikeue , Feng Chen , Tao Zhang , Fengxian Qiu , Toshiharu Teranishi , Songlin Xue . Local aromatic ring cleaves the global aromatic ring in hexaphyrin(2.1.2.1.2.1). Chinese Chemical Letters, 2025, 36(7): 110435-. doi: 10.1016/j.cclet.2024.110435
15. [15]
  Yuexiang Liu , Xiangqiao Yang , Tong Lin , Guantian Yang , Xiaoyong Xu , Bubing Zeng , Zhong Li , Weiping Zhu , Xuhong Qian . Efficient continuous synthesis of 2-[3-(trifluoromethyl)phenyl]malonic acid, a key intermediate of Triflumezopyrim, coupling with esterification-condensation-hydrolysis. Chinese Chemical Letters, 2025, 36(1): 109747-. doi: 10.1016/j.cclet.2024.109747
16. [16]
  Fuyun Chi , Man Zhang , Yiman Han , Fukui Shen , Shijie Peng , Bo Su , Yuanyuan Hou , Gang Bai . Covalent modulation of mPGES1 activity via α,β-unsaturated aldehyde group: Implications for downregulating PGE2 expression and antipyretic response. Chinese Chemical Letters, 2025, 36(4): 109913-. doi: 10.1016/j.cclet.2024.109913
17. [17]
  Chengyao Zhao , Jingyuan Liao , Yuxiang Zhu , Yiying Zhang , Lianjie Zhai , Junrong Huang , Hengzhi You . Polystyrene-supported phosphoric-acid catalyzed atroposelective construction of axially chiral N-aryl benzimidazoles. Chinese Chemical Letters, 2025, 36(6): 110337-. doi: 10.1016/j.cclet.2024.110337
18. [18]
  Qi Wei , Hua Xin , Xiaolong Wang , Changjuan Qin , Yuanzhen Su , Di Li , Jianxun Ding . Unimolecular chiral poly(amino acid)s as adjuvants of nanovaccines for augmented cancer immunotherapy. Chinese Chemical Letters, 2025, 36(11): 111477-. doi: 10.1016/j.cclet.2025.111477
19. [19]
  Xinlong Han , Huiying Zeng , Chao-Jun Li . Trifluoromethylative homo-coupling of carbonyl compounds. Chinese Chemical Letters, 2025, 36(1): 109817-. doi: 10.1016/j.cclet.2024.109817
20. [20]
  Hongjin Xu , Jinghua Wu , Hui Wang , Huanfeng Jiang , Zhiqiang Ma . Asymmetric total synthesis of (–)-14-epi-sinugyrosanolide A. Chinese Chemical Letters, 2026, 37(3): 112018-. doi: 10.1016/j.cclet.2025.112018

Get Citation

PDF

XML

Metrics

PDF Downloads(1)
Abstract views(1321)
HTML views(25)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Address：Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888

DownLoad: Full-Size Img PowerPoint

Return