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DOI:10.1021/ol5036613 - Corpus ID: 21250068
@article{Shi2015PdcatalyzedAI, title={Pd-catalyzed asymmetric intramolecular aryl C-O bond formation with SDP(O) ligand: enantioselective synthesis of (2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanols.}, author={Jialing Shi and Ting Wang and Yusha Huang and Xinhao Zhang and Yundong Wu and Qian Cai}, journal={Organic letters}, year={2015}, volume={17 4}, pages={ 840-3 }, url={https://api.semanticscholar.org/CorpusID:21250068}}
- Jialing Shi, Ting Wang, Q. Cai
- Published in Organic Letters 6 February 2015
- Chemistry
The protocol provides an efficient and highly enantioselective method for the synthesis of 2-hydroxymethyl-1,4-benzodioxanes and density functional theory studies provide a model that accounts for the origin of the enantiOSElectivity.
30 Citations
30 Citations
- Jialing ShiTing WangYusha HuangXinhao ZhangYundong WuQ. Cai
- 2015
Chemistry
The method has been successfully applied in the syntheses of selective 5-HT1A receptor agonist MKC-242 (VIIIa) and selective α1D-adrenoceptor inhibitor WB4101 (VIIIb).
- Xuguang YinYi Huang Xumu Zhang
- 2018
Chemistry
Organic letters
Rh-catalyzed asymmetric hydrogenation of various benzo[ b][1,4]dioxine derivatives was successfully developed and applied to develop highly efficient synthetic routes for the construction of some important biologically active molecules, such as MKC-242, WB4101, BSF-190555, and ( R)-doxazosin·HCl.
- 20
- Jinhui CaiZhen-Kai WangMuhammad UsmanZhiwu LuXu‐Dong HuWen-Bo Liu
- 2019
Chemistry
Organic letters
A copper-catalyzed efficient enantioselective construction of chiral quaternary carbon-containing chromanes and 3,4-dihydropyrans is reported. The desymmetric C-O coupling is enabled by a chiral…
- 4
- Yanzhao WangJingzhao XiaGuoqiang YangWanbin Zhang
- 2018
Chemistry
- 18
- Yong ZhangQiu-Ying Wang Q. Cai
- 2017
Chemistry
The Journal of organic chemistry
An enantioselective desymmetric aryl C-O coupling reaction was demonstrated under the catalysis of CuI and a chiral cyclic diamine ligand and a series of chiral oxygen-containing heterocyclic units with tertiary or quaternary stereocarbon centers were synthesized with this method.
- 11
- Wenqiang YangYangyuan LiuShasha ZhangQ. Cai
- 2015
Chemistry
Angewandte Chemie
A broad range of substrates are compatible with this Cu(I)-diamine catalytic system and afford the desired coupling products with chiral tertiary or quaternary carbon centers in high yields and good to excellent enantioselectivities under mild conditions.
- 36
- N. HuKe LiZheng WangWenjun Tang
- 2016
Chemistry
Angewandte Chemie
The application of this method to the synthesis of the chiral chroman backbone of α-tocopherol was demonstrated and the sterically bulky and conformationally well defined chiral monophosphorus ligand L4 or L5 was responsible for the high reactivity and enantioselectivity of these transformations.
- 75
- Quan-Quan ZhouFu‐Dong LuDan LiuLiang‐Qiu LuW. Xiao
- 2018
Chemistry
1,4-Benzodioxane widely exists as the core structure in many therapeutic agents and bioactive natural compounds. Hence, to access this kind of molecule, an enantioselective desymmetric C–O cross…
- 17
- PDF
- Muliang ZhangRehanguli RuziNan LiJin XieChengjian Zhu
- 2018
Chemistry
A practical photoredox and cobalt co-catalyzed C(sp2)–H functionalization/C–O bond formation is described herein, with dihydrogen as the only by-product. A variety of lactone products can be…
- 22
- PDF
- Liu YangH. Lu D. Xue
- 2020
Chemistry
Angewandte Chemie
A highly effective C-O coupling reaction of (hetero)aryl electrophiles with primary and secondary alcohols is reported, affording synthetically important ethers.
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58 References
- Wenqiang YangJiajie Yan Q. Cai
- 2013
Chemistry
Organic letters
The intramolecular asymmetric aryl C-O coupling reactions of 2-(2-haloaryl)propane-1,3-diols led to the enantioselective formation of chiral (3,4-dihydro-2H-chromen-3-yl)methanols in good yields and high enantiomeric selectivity.
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Chemistry
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Chemistry
Organic letters
2,3-Dihydro-1,4-benzodioxins can be prepared in a tandem one-pot procedure by reaction of o-iodophenols with epoxides catalyzed by Cu2O/1,10-phenanthroline/Cs2CO3 system, giving moderate to good yields.
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Chemistry
Angewandte Chemie
DFT studies provide a model which successfully accounts for the origin of enantioselectivity and the cyano group at the prochiral center plays a key role for the high enantiosity and works as an important functional group for further transformations.
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- 2001
Chemistry
Journal of the American Chemical Society
A number of oxygen heterocycles were synthesized using the palladium-catalyzed intramolecular etherification of aryl halides by employing di-tert-butylphosphinobiaryl ligands, an antidepressant currently in clinical trials.
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- 2001
Chemistry
Organic letters
It is demonstrated that both 1,2,2-2,6,6-pentamethylpiperidine and 1,4-dioxane can act as hydride donors in palladium-catalyzed polyene cyclizations of 2 and 3 and is the best substitute for PMP.
- 18
- Masayoshi NakojiTakatoshi KanayamaTomotaka OkinoY. Takemoto
- 2002
Chemistry
The Journal of organic chemistry
Pd-catalyzed asymmetric allylic alkylation of the glycine imino ester 1a has been developed using a chiral quaternary ammonium salt 3d without chiral phosphine ligands to achieve high enantioselectivity.
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- Jeffrey S. CannonAngela OlsonL. OvermanNicole S. Solomon
- 2012
Chemistry
The Journal of organic chemistry
2-Vinylchromanes can be prepared in good yields and high enantiomeric purities from analogous (E)-allylic acetate precursors, which constitutes the first report that acetate is a competent leaving group in COP-catalyzed enantioselective S(N)2' substitution reactions.
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- PDF
- A. VorogushinXiaohua HuangS. Buchwald
- 2005
Chemistry
Journal of the American Chemical Society
The efficient coupling of a number of unactivated aryl chlorides and bromides with cyclic and acyclic secondary alcohols was achieved, including the coupling of allylic alcohols for the first time in a Pd-catalyzed coupling process.
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- O. KitagawaM. Yoshikawa T. Taguchi
- 2006
Chemistry
Journal of the American Chemical Society
In the presence of (R)-DTBM-SEGPHOS-Pd(OAc)(2) catalyst, N-arylation of various o-tert-butylanilides with p-iodonitrobenzene proceeds with high enantioselectivity to give atropisomeric N-(p-nitrophenyl)anilides having an N-C chiral axis in good yields.
- 103
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