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29 results on '"Jin, Shicheng"'

19. Enzyme-Inspired Chiral Secondary-Phosphine-Oxide Ligand with Dual Noncovalent Interactions for Asymmetric Hydrogenation

Author

Chen, Caiyou, Zhang, Zhefan, Jin, Shicheng, Fan, Xiangru, Geng, Mingyu, Zhou, Yan, Wen, Songwei, Wang, Xinrui, Chung, Lungwa, Dong, Xiuqin, Zhang, Xumu, Chen, Caiyou, Zhang, Zhefan, Jin, Shicheng, Fan, Xiangru, Geng, Mingyu, Zhou, Yan, Wen, Songwei, Wang, Xinrui, Chung, Lungwa, Dong, Xiuqin, and Zhang, Xumu

Abstract

Inspired by the unique character of enzymes, we developed novel chiral SPO (secondary-phosphine-oxide) ligand (SPO-Wudaphos) which can enter into both ion pair and H-bond noncovalent interactions. The novel chiral SPO-Wudaphos exhibited excellent results in the asymmetric hydrogenation of α-methylene-γ-keto carboxylic acids, affording the chiral γ-keto acids with up to over 99 % ee. A series of control experiments and DFT calculations were conducted to illustrate the critical roles of both the ion pair and H-bond noncovalent interactions. © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Published
2017

27. Divergent Total Syntheses of Napelline-Type C20-Diterpenoid Alkaloids: (-)-Napelline, (+)-Dehydronapelline, (-)-Songorine, (-)-Songoramine, (-)-Acoapetaldine D, and (-)-Liangshanone.

Author

Jin S, Zhao X, and Ma D

Subjects
Aconitine, Octanes, Stereoisomerism, Alkaloids, Diterpenes, Diterpenes, Kaurane
Abstract

The napelline-type alkaloids possess an azabicyclo[3.2.1]octane moiety and an ent -kaurane-type tetracyclic skeleton (6/6/6/5) along with varied oxidation patterns embedded in the compact hexacyclic framework. Herein, we disclose a divergent entry to napelline-type alkaloids that hinges on convergent assembly of the ent -kaurane core using a diastereoselective intermolecular Cu-mediated conjugate addition and subsequent intramolecular Michael addition reaction as well as rapid construction of the azabicyclo[3.2.1]octane motif via an intramolecular Mannich cyclization. The power of this strategy has been demonstrated through efficient asymmetric total syntheses of eight napelline-type alkaloids, including (-)-napelline, (-)-12- epi -napelline, (+)-dehydronapelline, (+)-12- epi -dehydronapelline, (-)-songorine, (-)-songoramine, (-)-acoapetaldine D, and (-)-liangshanone.

Published
2022
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28. Sequence-Dependent Stereodivergent Allylic Alkylation/Fluorination of Acyclic Ketones.

Author

Liu XJ, Jin S, Zhang WY, Liu QQ, Zheng C, and You SL

Abstract

The stereodivergent iridium-catalyzed allylic alkylation and fluorination of acyclic ketones is described. α-Pyridyl-α-fluoroketones with vicinal tertiary and quaternary stereocenters were obtained in moderate to excellent yields and stereoselectivities. Distinct from known stereodivergent synthesis, for which two different chiral catalysts are required in general, herein we report a sequence-dependent stereodivergent synthesis. With only a single chiral Ir catalyst, all four possible stereoisomers of the products were prepared from the same starting materials by simply adjusting the sequence of asymmetric allylic alkylation and fluorination and varying the absolute configuration of the Ir catalyst., (© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)

Published
2020
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29. Enzyme-Inspired Chiral Secondary-Phosphine-Oxide Ligand with Dual Noncovalent Interactions for Asymmetric Hydrogenation.

Author

Chen C, Zhang Z, Jin S, Fan X, Geng M, Zhou Y, Wen S, Wang X, Chung LW, Dong XQ, and Zhang X

Abstract

Inspired by the unique character of enzymes, we developed novel chiral SPO (secondary-phosphine-oxide) ligand (SPO-Wudaphos) which can enter into both ion pair and H-bond noncovalent interactions. The novel chiral SPO-Wudaphos exhibited excellent results in the asymmetric hydrogenation of α-methylene-γ-keto carboxylic acids, affording the chiral γ-keto acids with up to over 99 % ee. A series of control experiments and DFT calculations were conducted to illustrate the critical roles of both the ion pair and H-bond noncovalent interactions., (© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)

Published
2017
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