Interrupted Michael Reaction: Sulfophosphinoylation of α,β-Unsaturated Ketones Catalyzed by Phosphine DOI
Xiaohong Wei,

Ya-Wen Xue,

Xuan Liu

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(22), P. 16564 - 16570

Published: Oct. 31, 2024

An efficient method for phosphine-catalyzed sulfophosphinoylation of α,β-unsaturated ketones synthesis allylic organophosphorus compounds has been reported, in which acting as zwitterions react with electrophiles and nucleophiles to form a C-P bond C-O obtain high regio- stereoselectivity moderate excellent yields.

Language: Английский

Asymmetric Construction of Bis‐Spirocyclic Pyrazolones Bearing Vicinal Quaternary Carbon Centers DOI
Mengjie Yang,

Aiqi Xue,

Xingfu Wei

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(25)

Published: April 8, 2024

Abstract A catalytic asymmetric (3+2) cyclization of pyrazolone‐based MBH adducts with alkylidenyl isoxazolones was presented by using DMAP‐derived chiral catalyst, affording bis‐spirocyclic pyrazolones bearing vicinal all‐carbon quaternary stereocenters within an imbedded cyclopentene ring scaffold in good yields excellent stereoselectivities under mild conditions.

Language: Английский

Citations

1
Synthesis of Chiral Spiro[oxindole-3,2′-pyrrolidine] Derivatives Integrated with Spiro Indane-1,3-dione and Trifluoromethyl Group Pharmacophores via Organocatalyzed Asymmetric [3+2] Annulation DOI

Zhenghong Zhou,

Li Fei, Zhuo Li

et al.

Synthesis, Journal Year: 2022, Volume and Issue: 55(09), P. 1427 - 1440

Published: Dec. 6, 2022

Abstract A mild and efficient organocatalyzed [3+2] cycloaddition of isatin-derived ketimines 2-ylideneindane-1,3-diones has been realized. The resulting spiro[oxindole-3,2′-pyrrolidine]s bearing both a spiro indane-1,3-dione motif trifluoromethyl group were obtained in high yields with good diastereo- enantioselectivities.

Language: Английский

Citations

5
An Efficient Route to Access Spirooxindole–Pyrazolone-Fused Cyclopentenes by a Diastereoselective [3+2] Annulation DOI
Ramakrishna G. Bhat,

Abhijeet S. Sabale,

Prakash K. Warghude

et al.

Synlett, Journal Year: 2023, Volume and Issue: 34(14), P. 1732 - 1738

Published: Jan. 16, 2023

Abstract A DMAP-catalyzed, highly diastereoselective, [3+2] cycloaddition of pyrazolone-derived Morita–Baylis–Hillman carbonates to 3-methyleneoxindoles has been developed. variety structurally diverse and complex spiropyrazolone-fused oxindoles bearing three contiguous chiral centers have synthesized in high yields (up 98%) with excellent diastereoselectivities 99:1). Moreover, the synthetic potential this protocol demonstrated by performing a Suzuki coupling reaction.

Language: Английский

Citations

2
Bifunctional Squaramide‐Catalyzed Asymmetric [3+2] Annluation Reactions of 2‐Isothiocyanato‐1‐indanones with 2‐Arylidene‐1,3‐indanediones DOI

Jiang‐Song Zhai,

Donghua Xie,

Da‐Ming Du

et al.

ChemistrySelect, Journal Year: 2022, Volume and Issue: 7(37)

Published: Oct. 5, 2022

Abstract A squaramide‐catalyzed asymmetric Michael/cyclization tandem reaction between 2‐isothiocyanato‐1‐indanones and 2‐arylidene‐1,3‐indanediones was developed. Under this strategy, the corresponding chiral bispirocyclic indanone compounds containing two contiguous stereocenters were obtained under mild conditions in moderate to excellent yields (up 99 %) enantioselectivities 98 % ee). In addition, further transformation experiments achieved through oxidation methylation reactions of product, which also confirmed synthetic practicality strategy.

Language: Английский

Citations

3
Chemodivergent Parallel Kinetic Resolution of Paracyclophanes: Enantiomer Fishing with Different Substrates DOI Open Access
Qian Liu,

Kunpeng Teng,

Yi Zhang

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(46)

Published: July 25, 2024

Abstract An unprecedented chemodivergent strategy for parallel kinetic resolution (PKR) is disclosed through which two planar chiral products bearing different structures were simultaneously afforded with opposite stereoselectivities. Two achiral esters are activated by one single N‐heterocyclic carbene (NHC) catalyst to react the enantiomers of racemic imine substrate in a fashion. distinct and stereoselectivities respectively from same reaction system good excellent yields, enantio‐ diastereoselectivities. Control experiments studies carried out probe dynamic properties during progress. The pyridine lactam show interesting applications both asymmetric synthesis pesticide development.

Language: Английский

Citations

0
Interrupted Michael Reaction: Sulfophosphinoylation of α,β-Unsaturated Ketones Catalyzed by Phosphine DOI
Xiaohong Wei,

Ya-Wen Xue,

Xuan Liu

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(22), P. 16564 - 16570

Published: Oct. 31, 2024

An efficient method for phosphine-catalyzed sulfophosphinoylation of α,β-unsaturated ketones synthesis allylic organophosphorus compounds has been reported, in which acting as zwitterions react with electrophiles and nucleophiles to form a C-P bond C-O obtain high regio- stereoselectivity moderate excellent yields.

Language: Английский

Citations

0