Feng Sha

Name: 沙风; Sha, Feng

Organization: East China University of Science and Technology , China

Department: Key Laboratory for Advanced Materials and Institute of Fine Chemicals

Title: Associate Professor(PhD)

Chemicals
References

Direct construction of xanthene and benzophenone derivatives via Brønsted acid controlled Diels-Alder reaction of 3-vinylchromones and arynes

Co-reporter:Xu-Jiao Huang, Yuan Tao, Yue-Kun Li, Xin-Yan Wu, Feng Sha

Tetrahedron 2016 Volume 72(Issue 52) pp:8565-8577

Publication Date(Web):29 December 2016

DOI:10.1016/j.tet.2016.11.028

A Brønsted acid controlled Diels-Alder reaction of 3-vinylchromones with arynes has been developed. By employing different kinds and amounts of acid, 9-aryl-9H-xanthen-9-ols or ortho-hydroxybenzophenones could be controllably furnished in good yields in an atom- and step-economic manner.

Enantioselective Vinylogous Michael/Cyclization Cascade Reaction of Acyclic ,-Unsaturated Amides with Isatylidene Malononitriles: Asymmetric Construction of Spirocyclic Oxindoles

Co-reporter:Tian-Ze Li;Jin Xie;Yu Jiang;Xin-Yan Wu

Advanced Synthesis & Catalysis 2015 Volume 357( Issue 16-17) pp:3507-3511

Publication Date(Web):

DOI:10.1002/adsc.201500469

Enantioselective Allylic Amination of Morita-Baylis-Hillman Acetates Catalyzed by Chiral Thiourea-Phosphine

Co-reporter:Xuan Zhao;Tianchen Kang;Jie Shen;Xinyan Wu

Chinese Journal of Chemistry 2015 Volume 33( Issue 12) pp:1333-1337

Publication Date(Web):

DOI:10.1002/cjoc.201500697

Abstract

The enantioselective allylic amination of Morita-Baylis-Hillman acetates catalyzed by chiral cyclohexane-based thiourea-phosphine catalysts was investigated. In the presence of 20 mol% rosin-derived thiourea-phosphine 3j, the chiral amines were obtained in up to 88% yield and up to 85% ee.

Enantioselective [4+2] cycloaddition reaction of α,β-unsaturated imine and methyl vinyl ketone catalyzed by chiral phosphine

Co-reporter:Ge Wang, Rukeya Rexiti, Feng Sha, Xin-Yan Wu

Tetrahedron 2015 Volume 71(Issue 24) pp:4255-4262

Publication Date(Web):17 June 2015

DOI:10.1016/j.tet.2015.04.076

New bifunctional phosphines were prepared as chiral organocatalysts for the enantioselective [4+2] cycloaddition between α,β-unsaturated imines and methyl vinyl ketone. In the presence of 10 mol % of amide-phosphine, the [4+2] cycloaddition reaction was achieved in good-to-excellent yields (up to 95%) and diastereoselectivities (up to 99:1 dr) with moderate-to-good enantioselectivities (up to 82% ee). This methodology establishes a new protocol for the asymmetric construction of functionalized tetrahydropyridines.

Construction of Benzo[c]carbazoles and Their Antitumor Derivatives through the Diels–Alder Reaction of 2-Alkenylindoles and Arynes

Co-reporter:Feng Sha, Yuan Tao, Chen-Yu Tang, Fei Zhang, and Xin-Yan Wu

The Journal of Organic Chemistry 2015 Volume 80(Issue 16) pp:8122-8133

Publication Date(Web):July 23, 2015

DOI:10.1021/acs.joc.5b01223

The direct assembly of benzo[c]carbazole derivatives via the Diels–Alder reaction of arynes and easily accessible 2-alkenylidoles was reported. By employing different aryne precursor loads, 6,7-dihydrobenzo[c]carbazoles or aryl-substituted 7,11b-dihydrobenzo[c]carbazoles could be controllably generated in good to excellent yields under a nitrogen atmosphere. On the other hand, when the reaction was conducted under oxygen, oxidated/aromatized product benzo[c]carbazoles could be generated directly with high selectivity and efficiency in a one-step manner. Interestingly, the benzo[c]carbazole-5-carboxamide amidation derivatives of the above products showed good antitumor activities. The inhibitory effect of these molecules against cancer cells was also described.

Rhodium(III)-Catalyzed Direct C-2 Olefination of Unactivated Indoles Utilizing OH/NH2 as Directing Group

Co-reporter:Chen-Yu Tang;Yuan Tao;Xin-Yan Wu

Advanced Synthesis & Catalysis 2014 Volume 356( Issue 2-3) pp:609-615

Publication Date(Web):

DOI:10.1002/adsc.201300930

Cover Picture: Direct Assembly of Benzo[a]carbazole-5-carboxylates via a DielsAlder Reaction with Arynes and 3-Alkenylindoles (Asian J. Org. Chem. 12/2014)

Co-reporter:Yuan Tao;Fei Zhang;Chen-Yu Tang;Dr. Xin-Yan Wu;Dr. Feng Sha

Asian Journal of Organic Chemistry 2014 Volume 3( Issue 12) pp:

Publication Date(Web):

DOI:10.1002/ajoc.201490025

Direct Assembly of Benzo[a]carbazole-5-carboxylates via a DielsAlder Reaction with Arynes and 3-Alkenylindoles

Co-reporter:Yuan Tao;Fei Zhang;Chen-Yu Tang;Dr. Xin-Yan Wu;Dr. Feng Sha

Asian Journal of Organic Chemistry 2014 Volume 3( Issue 12) pp:1292-1301

Publication Date(Web):

DOI:10.1002/ajoc.201402152

Abstract

A concise and direct synthetic strategy for the construction of benzo[a]carbazole-5-carboxylates has been disclosed via the Diels–Alder reaction of arynes and 3-alkenylindoles. The reaction is highly selective and affords the benzo[a]carbazole-5-carboxylates in good-to-excellent yields.

Pd-catalyzed assembly of phenanthridines from aryl ketone O-acetyloximes and arynes through C–H bond activation

Co-reporter:Chen-Yu Tang, Xin-Yan Wu, Feng Sha, Fei Zhang, Hao Li

Tetrahedron Letters 2014 Volume 55(Issue 5) pp:1036-1039

Publication Date(Web):29 January 2014

DOI:10.1016/j.tetlet.2013.12.075

Pd-catalyzed annulation of aryne and aryl ketone O-acetyloxime via C–H bond activation was realized. Through the C–H bond activation/insertion/cyclization/elimination reaction sequence, phenanthridines are successfully constructed, providing an attractive strategy to approach substituted heterocycle without preactivation of starting materials.

One-pot synthesis of α-fluoro-β-amino acid and indole spiro-derivatives via CN bond cleavage/formation

Co-reporter:Chen-Yu Tang, Ge Wang, Xue-Yan Yang, Xin-Yan Wu, Feng Sha

Tetrahedron Letters 2014 Volume 55(Issue 47) pp:6447-6450

Publication Date(Web):19 November 2014

DOI:10.1016/j.tetlet.2014.09.130

In this Letter, the α-fluoro-β-amino acid directives were elegantly generated via a novel strategy of the nucleophilic addition of arynes and aziridines. CN bonds were successfully constructed with high efficiency. With the utilization of TABF hydrate as the fluorinated reagent, fluorine atom could be assembled into the target molecule selectively. Interestingly, under another condition, unexpected indole spiro-derivatives could be achieved successfully.

Organocatalyzed Enantioselective Mannich Reaction of Pyrazoleamides with Isatin-Derived Ketimines

Co-reporter:Tian-Ze Li, Xi-Bo Wang, Feng Sha, and Xin-Yan Wu

The Journal of Organic Chemistry 2014 Volume 79(Issue 10) pp:4332-4339

Publication Date(Web):April 15, 2014

DOI:10.1021/jo500145w

The first organocatalytic enantioselective Mannich reaction of pyrazoleamides with isatin-derived N-Boc ketimines has been developed to afford 2-oxindole-based chiral β-amino amides in good yields (84–97%) with excellent diastereo- and enantioselectivities (up to 99:1 dr and >99% ee).

Highly Regioselective Assembly of Di- or Trisubstituted Pyridines from Arynes, Isocyanides, and 3-Bromo- or 3-Acetoxypropynes

Co-reporter:Feng Sha;Hui Shen ;Xin-Yan Wu

European Journal of Organic Chemistry 2013 Volume 2013( Issue 13) pp:2537-2540

Publication Date(Web):

DOI:10.1002/ejoc.201300001

Abstract

A facile synthetic method for the preparation of di- and trisubstituted pyridines with high regioselectivity through an intramolecular pericyclization strategy is disclosed. The multicomponent reaction of isocyanides, arynes, and 3-bromopropyne affords disubstituted pyridines in good yields. In contrast, the use of 3-acetoxypropyne results in the formation of trisubstituted pyridines through intramolecular pericyclization of an in situ formed azatriene. In this way, desirable pyridines can be constructed in a one-pot manner.