Enantioselective Total Synthesis of (+)‐Propolisbenzofuran B† DOI
Wenxiu Xu,

Li‐Han Zhao,

Yao Zhu

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(22), P. 2833 - 2839

Published: July 22, 2024

Comprehensive Summary The first catalytic asymmetric total synthesis of (+)‐propolisbenzofuran B, enabled by a highly enantioselective rhodium‐catalyzed hydrogenation tetrasubstituted olefin, was described. Other noteworthy aspects include the construction central hydrodibenzo[ b , d ]furan core through sequence Zn(II)‐mediated regioselective benzofuran formation and Dieckmann condensation, as well C‐H oxidations, involving visible light‐induced Fe(III)‐catalyzed benzylic C(sp 3 )‐H oxidation. Additionally, absolute configuration confirmed X‐ray analysis carbonate intermediate.

Language: Английский

A concise review on recent advances in catalytic asymmetric hydrogenation DOI
Priyanka Behera,

D. S. Ramakrishna,

Manchikanti M. Chandrasekhar

et al.

Chirality, Journal Year: 2023, Volume and Issue: 35(8), P. 477 - 497

Published: March 24, 2023

Abstract Accounts on the recent (over past 10 years) catalytic asymmetric hydrogenation reaction‐based achievements with different catalysts to generate natural products and synthetic targets such as fragrances, pharmaceutical agents, agrochemicals are mentioned in this present concise review. Mechanistic steps, chemoselectivity higher functional group tolerance by employing transition metal‐based chiral (Ir‐, Rh‐, Ni‐, Ru‐, Fe‐, Mn‐, Pd‐, Co‐, Zn‐based organometallic complexes), biocatalysts their importance genesis of chirality coupled turnover numbers also described.

Language: Английский

Citations

23
Recent advances in the metal-catalyzed asymmetric alkene hydrogenation of cyclic conjugated carbonyl compounds DOI
Min Tan, Bram B. C. Peters, Pher G. Andersson

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(10), P. 2934 - 2953

Published: Jan. 1, 2024

This review summarizes the recent advances (2016–2023) in stereoselective metal-catalyzed hydrogenation of cyclic α,β-unsaturated ketones, lactams and lactones since considerable developments were made. Where possible application these methodologies synthesis is outlined.

Language: Английский

Citations

7
Cyclolignan synthesis streamlined by enantioselective hydrogenation of tetrasubstituted olefins DOI
Wenxiu Xu, Zhuo Peng,

Qing‐Xiu Gu

et al.

Nature Synthesis, Journal Year: 2024, Volume and Issue: 3(8), P. 986 - 997

Published: June 20, 2024

Language: Английский

Citations

7
IPTG‐induced high protein expression for whole‐cell biosynthesis of L‐phosphinothricin DOI

Jian‐Miao Xu,

Zhou‐Sheng Wu,

Ke‐Ji Zhao

et al.

Biotechnology Journal, Journal Year: 2023, Volume and Issue: 18(9)

Published: June 2, 2023

Biocatalytic production of L-phosphinothricin (L-PPT) is currently the most promising method. In this work, we use an Escherichia coli strain coexpressing D-amino acid oxidase and catalase (E. DAAO-CAT) to oxidation biocatalytic D-PPT PPO, then second E. glutamate dehydrogenase formate GluDH-FDH) reduce PPO L-PPT.We compared effects different concentrations IPTG or lactose on protein expression enzyme activity in 5 L fermenter. The best induction conditions for DAAO-CAT were 0.05 mM IPTG, 18 h at 28°C. specific activities DAAO CAT 153.20 U g-1 896.23 , respectively. optimal GluDH-FDH 0.2 19 GluDH FDH 41.72 109.70 200 was biocatalyzed by 4 with space-time yield 9.0 g·L-1 ·h-1 conversion rate over 99.0%. Then 220 converted L-PPT 3 14.5 To our knowledge, efficient reaction production.We found that has advantages biomass GluDH-FDH, more environmentally friendly. Our data implicated can replace terms economic feasibility effectiveness scaled-up industrial fermentations.

Language: Английский

Citations

13
Asymmetric Formal Synthesis of (−)-Paroxetine DOI
Lei Liu,

Xianjing Zhou,

Wen-Feng Huang

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: May 19, 2025

A concise, asymmetric formal synthesis of (-)-paroxetine is reported. The synthetic strategy features an hydrogenation for constructing the chiral center and a phosphate-group-involved intramolecular SN2 reaction construction trans-3,4-disubstituted piperidine scaffold. This route concise practical synthesis.

Language: Английский

Citations

0
Asymmetric hydrogenation of all-carbon tetrasubstituted α-acylpyrazole-β-alkyl cycloalkenes DOI
Minjie Zhang, Peng Cui, Kai Zhang

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(20), P. 5070 - 5075

Published: Jan. 1, 2023

A general method for Ir-catalyzed asymmetric hydrogenation of tetrasubstituted α-acylpyrazole-β-alkyl cycloalkenes has been developed, furnishing 1,2- cis substituted carbo- or heterocycles with high yields and excellent enantioselectivities.

Language: Английский

Citations

5
Rhodium(CAAC)‐Catalyzed Arene Hydrogenation of Benzo‐Fused N‐Heterocycles to Saturated Building Blocks with an all‐cis Configuration DOI Creative Commons

Christian H. Schiwek,

Simone Stegbauer,

Thomas Pickl

et al.

Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(19), P. 3360 - 3365

Published: July 12, 2022

Abstract Saturated carbo‐ and heterocyclic building blocks can be readily obtained by the hydrogenation of aromatic heterocycles. Although a variety methods have been established to accomplish this transformation for simple arenes, N ‐heterocycles is less explored. We herein report diastereoselective arene which was applied an array benzo‐fused ‐heterocycles. A total 48 saturated heterocycles in presence rhodium complex Cy (CAAC)Rh(cod)Cl yields 72–98% with moderate high diastereoselectivities exhibiting hydrogen atoms all‐ cis arrangement. The tolerance towards functional groups enables formation valuable products, offer starting point further derivatization. magnified image

Language: Английский

Citations

7
Reduction: Hydrogenation and Transfer Hydrogenation of C=C DOI
Masaki Tsukamoto, Kin‐ichi Oyama

Elsevier eBooks, Journal Year: 2023, Volume and Issue: unknown, P. 266 - 287

Published: April 13, 2023

Language: Английский

Citations

1
Rhodium‐Catalyzed Asymmetric Hydrogenation of Tetrasubstituted α,β‐Unsaturated Amides: Efficient Access to Chiral β‐Amino Amides† DOI
Bing Jiao, Fangyuan Wang, Hui Lv

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(21), P. 2641 - 2646

Published: July 4, 2024

Comprehensive Summary The first asymmetric hydrogenation of acyclic tetrasubstituted α,β‐unsaturated amides has been achieved by using Rh/DuanPhos complex as a catalyst, delivering chiral β‐amino with two contiguous centers in excellent yields and high enantioselectivities (up to 99% yield, 96% ee), which provides efficient concise access valuable amide derivatives. gram‐scale reaction transformation acid cyanide demonstrated the utility this methodology.

Language: Английский

Citations

0
Enantioselective Total Synthesis of (+)‐Propolisbenzofuran B† DOI
Wenxiu Xu,

Li‐Han Zhao,

Yao Zhu

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(22), P. 2833 - 2839

Published: July 22, 2024

Comprehensive Summary The first catalytic asymmetric total synthesis of (+)‐propolisbenzofuran B, enabled by a highly enantioselective rhodium‐catalyzed hydrogenation tetrasubstituted olefin, was described. Other noteworthy aspects include the construction central hydrodibenzo[ b , d ]furan core through sequence Zn(II)‐mediated regioselective benzofuran formation and Dieckmann condensation, as well C‐H oxidations, involving visible light‐induced Fe(III)‐catalyzed benzylic C(sp 3 )‐H oxidation. Additionally, absolute configuration confirmed X‐ray analysis carbonate intermediate.

Language: Английский

Citations

0