Direct construction of chiral quaternary dihydropyranones through highly enantioselective organocatalytic hetero-Diels–Alder reactions of olefinic azlactones

Literature Information

Publication Date 2016-03-03
DOI 10.1039/C6QO00018E
Impact Factor 5.281
Authors

Tai-Ping Gao, Dan Liu, Jun-Bing Lin, Xiu-Qin Hu, Zhu-Yin Wang, Peng-Fei Xu


View Original

Abstract

The first organocatalytic hetero-Diels–Alder reaction of an in situ generated diene with either α-keto esters or β,γ-unsaturated α-keto esters was successfully developed. The densely functionalized dihydropyranones with a highly congested quaternary center were readily obtained in moderate to good yields with excellent enantioselectivities under mild conditions.

Related Literature

Synthesis and properties of heterografted toothbrush-like copolymers with alternating PEG and PCL grafts and tunable RAFT-generated segments

Dandan Tang, Xiao Jiang, Huanhuan Liu, Cangxia Li, Youliang Zhao

2014-05-27 Paper

DOI: 10.1039/C4PY00332B

Biostable and bioreducible polymersomes for intracellular delivery of doxorubicin

Thavasyappan Thambi, V. G. Deepagan, Hyewon Ko, Gi-Ra Yi, Jun Young Lee, Doo Sung Lee

2014-05-14 Paper

DOI: 10.1039/C4PY00567H

New method for the synthesis of fully aliphatic telechelic α,ω-dihydroxy-polyisobutylene

Marcela Castano, Matthew L. Becker

2014-06-11 Paper

DOI: 10.1039/C4PY00569D

Highly pH-sensitive polyurethane exhibiting shape memory and drug release

Ying Li, Ye Liu, Tao Gong, Lin Wang, Shaobing Zhou

2014-05-02 Paper

DOI: 10.1039/C4PY00474D

Photoswitchable nanocomposites made from coumarin-functionalized cellulose nanocrystals

Mahesh V. Biyani, Christoph Weder, E. Johan Foster

2014-06-04 Paper

DOI: 10.1039/C4PY00486H

Reactive macromolecular micelle crosslinked highly elastic hydrogel with water-triggered shape-memory behaviour

Tingting Zhao, Mei Tan, Yulin Cui, Chao Deng, He Huang, Mingyu Guo

2014-05-07 Paper

DOI: 10.1039/C4PY00554F

Trehalose-functionalized block copolymers form serum-stable micelles

Swapnil R. Tale, Ligeng Yin, Theresa M. Reineke

2014-04-29 Paper

DOI: 10.1039/C4PY00399C

Synthesis and characterization of isosorbide-based polyphosphonates as biobased flame-retardants

Timothy C. Mauldin, Jeffrey W. Gilman, John R. Shields, Dylan J. Boday

2014-06-02 Paper

DOI: 10.1039/C4PY00591K

SET-LRP of semifluorinated acrylates and methacrylates

Shampa R. Samanta, Ruilong Cai, Virgil Percec

2014-05-27 Paper

DOI: 10.1039/C4PY00635F

You might also like

Compound Q&A

What is Ethyl 3-cyclohexylpropanoate (CAS: 10094-36-7)?

Ethyl 3-cyclohexylpropanoate is a clear, colorless to light yellow liquid with a...

10094-36-7Ethyl 3-cyclohexylpr...
Compound Q&A

How should waste containing 2-(Hydroxymethyl)-5-(methoxycarbonyl)-6-methyl-4-(2-nitrophenyl)nicotinic acid (CAS: 34783-31-8) be handled?

Waste containing 2-(Hydroxymethyl)-5-(methoxycarbonyl)-6-methyl-4-(2-nitrophenyl...

34783-31-82-(Hydroxymethyl)-5-...
Compound Q&A

How should waste containing 2,4,6-Tris(pentafluoroethyl)-1,3,5-triazine (CAS: 858-46-8) be handled?

Waste containing 2,4,6-Tris(pentafluoroethyl)-1,3,5-triazine (CAS: 858-46-8) sho...

858-46-82,4,6-Tris(pentafluo...
Compound Q&A

What precautions should be taken when handling Chloroac-nle-oh (CAS: 56787-36-1)?

When handling Chloroac-nle-oh (CAS: 56787-36-1), it is essential to wear appropr...

56787-36-1Chloroac-nle-oh
Compound Q&A

What industries use Ethyl 6-phenylimidazo[2,1-b][1,3]thiazole-3-carboxylate (CAS: 752244-05-6)?

Ethyl 6-phenylimidazo[2,1-b][1,3]thiazole-3-carboxylate is primarily used in the...

752244-05-6Ethyl 6-phenylimidaz...
Compound Q&A

Are there alternatives to alpha-(2-Bromophenyl)benzylamine (CAS: 55095-15-3) in synthesis?

Alternatives to alpha-(2-Bromophenyl)benzylamine (CAS: 55095-15-3) in synthesis ...

55095-15-3alpha-(2-Bromophenyl...
Compound Q&A

How should waste containing 2-Chloro-5-methoxypyridine (CAS: 139585-48-1) be handled?

Waste containing 2-Chloro-5-methoxypyridine (CAS: 139585-48-1) should be managed...

139585-48-12-Chloro-5-methoxypy...
Compound Q&A

What industries use 1-(4-Methoxyphenyl)-2,5-dimethyl-1H-pyrrole (CAS: 5044-27-9)?

1-(4-Methoxyphenyl)-2,5-dimethyl-1H-pyrrole (CAS: 5044-27-9) is used in various ...

5044-27-91-(4-Methoxyphenyl)-...
Compound Q&A

Are there alternatives to 3-Bromo-5-(N-Boc)aminomethylisoxazole (CAS: 903131-45-3) in synthesis?

There are alternative reagents and compounds that can be used in the synthesis o...

903131-45-33-Bromo-5-(N-Boc)ami...
Compound Q&A

What is Tungsten(IV) oxide (CAS: 12036-22-5)?

Tungsten(IV) oxide, also known as tungsten dioxide, is a chemical compound with ...

12036-22-5Tungsten(IV) oxide

Source Journal

Organic Chemistry Frontiers

Organic Chemistry Frontiers
CiteScore: 7.8
Self-citation Rate: 8.7%
Articles per Year: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

Recommended Compounds

Recommended Suppliers

Disclaimer
This page provides academic journal information for reference and research purposes only. We are not affiliated with any journal publishers and do not handle publication submissions. For publication-related inquiries, please contact the respective journal publishers directly.
If you notice any inaccuracies in the information displayed, please contact us at support@chemtradehub.com. We will promptly review and address your concerns.