24. Taming Chiral Quaternary Stereocenters via Remote H-Bonding Stereoinduction in Palladium-Catalyzed (3+2) Cycloadditions
Xiao, Y.-Q.; Li, M.-M.; Zhou, Z.-X.; Li, Y.-J. Cao, M.-Y.; Liu, X.-P.; Lu, H.-H.; Rao, L.*; Lu, L.-Q.*; Beauchemin, A. M.; Xiao, W.-J. Angew. Chem. Int. Ed. 2022, DOI: 10.1002/anie.202212444.
A new application of our Trost-type ligands (Thanks Liang-Qiu!)
The first palladium-catalyzed highly diastereo- and enantioselective (3+2) cycloaddition of vinyl cyclopropanes bearing two different electron-withdrawing groups
23. Concise Total Synthesis of Salimabromide
Lu, H.-H.*; Gan, K.-G.; Ni, F.-Q.; Zhang, Z.; Zhu, Y. J. Am. Chem. Soc. 2022, 144, 18778-18783; DOI: 10.1021/jacs.2c08337.
Simutaneous construction of the unique benzo-fused [4.3.1] framework and the vicinal quaternary carboncenters via a HAT-mediated cyclization (Giese-Baran reaction)
A novel tandem oxidative reaction was developed to form the butyrolactone and enone moieties concurrently
22. Concise Enantioselective Total Synthesis of Daphenylline Enabled by an Intramolecular Oxidative Dearomatization
Cao, M.-Y.; Ma, B.-J.; Gu, Q.-X.; Fu, B.; Lu, H.-H.* J. Am. Chem. Soc. 2022, 144, 5750-5755; DOI: 10.1021/jacs.2c01674.
The "hide-and-seek" thinking (might be uncontiously employed by synthetic chemists for synthesis design before) was proposed to help identify efficient synthesis routes
A novel oxidative dearomatization reaction of ester-tethered β-naphthol
An unprecedented remote acid-directed Mukaiyama-Michael reaction
A strategic tandem reductive amination/amidation double cyclization reaction
21. Nonafluorobutanesulfonyl Fluoride (Second Update)
Lu, H.-H.* Encyclopedia of Reagents for Organic Synthesis 2022; DOI: 10.1002/047084289X.rn061.pub3 (Invited).
20. Enantioselective Addition-Alkylation of α,β-Unsaturated Carbonyls via Bisguanidinium Silicate Ion Pair Catalysis
Chen, W.; Ang, E. C. X.; Tan, S. M.; Chua, Z.; Ren, J.; Yang, Z.; Teng, B.; Lee, R.*; Lu, H.-H.*; Tan, C.-H.* J. Am. Chem. Soc. 2020, 142, 19065-19070; DOI: 10.1021/jacs.0c00183.
Vicinal carbon stereocenters constructed with excellent selectivities (up to 99% ee, >99:1 dr)
Penta-coordinated silicates are crucial intermediates
19. Enantioselective Palladium-Catalyzed Decarboxylative Dearomative Asymmetric Allylic Alkylation of Benzofurans: Diversity-Oriented Synthesis of Flavaglines
Lu, H.-H.*; Cao, M.-Y. Sylett (Synpacts) 2021, 1981-1986; DOI: 10.1055/a-1650-4266 (Invited).
18. Optically Active Flavaglines-Inspired Molecules by a Palladium-Catalyzed Decarboxylative Dearomative Asymmetric Allylic Alkylation
Cao, M.-Y.; Ma, B.-J.; Lao, Z.-Q.; Wang, H.; Wang, J.; Liu, J.; Xing, K.; Huang, Y.-H.; Gan, K.-J.; Gao, W.; Wang, H.; Hong, X.; Lu, H.-H.* J. Am. Chem. Soc. 2020, 142, 12039-12045; DOI: 10.1021/jacs.0c05113.
A new class of Trost-type ligands bearing a chiral cycloalkane framwork
An unprecedented Pd-catalyzed dearomative AAA (> 30 examples, up to 96% ee)
A new blueprint for flavagline-based drug development by a DOS design
17. Catalytic Asymmetric Synthesis of a New Class of CyPHOX Ligands
Cao, M.-Y.; Xu, Z.-M.; Gao, W.; Liu, J.; Tan, F.*; Lu, H.-H.* Tetrahedron 2019, 75, 3282-3291; DOI: 10.1016/j.tet.2019.04.050.
Invited for Ryan Shenvi Award Issue
Four newly designed CyPHOX ligands with chiral cyclohexane scaffold replacing the previous planar aryl group of PHOX ligands, were efficiently prepared. The synthesis features a kinetically controlled asymmetric phos-Michael reactions of trisubstituted cyclic carboxylates, which is quite simple, reliable and scalable. Preliminary tests with our CyPHOX ligands showed that they exhibited better performance (44-67% ee) than the privileged PHOX ligand (13% ee) in Lam's nickel-catalyzed desymmetrizing arylative cyclization.
16. Witkin, J. M.*; Shenvi, R. A.; Li, X.; Gleason, S. D.; Weiss, J.; Morrow, D.; Catow, J. T.; Wakulchik, M.; Ohtawa, M.; Lu, H.-H.; Martinez, M. D.; Schkeryantz, J. M.; Carpenter, T. S.; Lightstone, F. C.; Cerne, R. Pharmacological characterization of the neurotrophic sesquiterpene jiadifenolide reveals a non-convulsant signature and potential for progression in neurodegenerative disease studies, Biochem. Pharm. 2018, 155, 61-70.
15. Lu, H.-H.; Pronin, S.; Antonova-Koch, Y.; Meister, S.; Winzeler, E. A.; Shenvi, R. A.* Synthesis of (+)-7,20-Diisocyanoadociane and Liver Stage Antiplas-modial Activity of the ICT Class, J. Am. Chem. Soc. 2016, 138, 7268-7271.
14. Lu, H.-H.; Martinez, M. D.; Shenvi, R. A.* An Eight-step, Gram-Scale Synthesis of (–)-Jiadifenolide, Nat. Chem. 2015, 7, 604-607.
- Highlighted in Chemistry World, July 27 2015;
- Highlighted by E. M. Carreira and M. Westph, Synfacts 2015, 11, 089;
- #1 most read article, June-July 2015.
13. Lu, H.-H.; Hinkelmann, B.; Tautz, T.; Li, J.; Franke, R.; Sasse, F.; Kalesse, M.* Paleo-Soraphens: Chemical Total Syntheses and Biological Studies, Org. Biomol. Chem. 2015, 13, 8029-8036.
12. Kalesse, M.*; Cordes, M.; Symkenberg, G.; Lu, H.-H. The Vinylogous Mukaiyama Aldol Reaction (VMAR) in Natural Product Synthesis, Nat. Prod. Rep. 2014, 31, 563-594.
11. Lu, H.-H.; Raja, A.; Franke, R.; Landsberg, D.; Sasse, F.; Kalesse, M.* Syntheses and Biological Evaluation of Paleo-Soraphens, Angew. Chem. Int. Ed. 2013, 52, 13549-13552.
10. Duan, S.-W.; Lu, H.-H.; Zhang, F.-G.; Xuan, J.; Chen, J.-R.; Xiao, W.-J.* Organocatalytic Conjugate Additions of Acetylacetone to 3-Ylideneoxindoles: A Direct Access to Highly Enantioenriched Oxindole Derivatives, Synthesis 2011, 1847-1852.
9. Lu, H.-H.; Tan, F.; Xiao, W.-J.* Enantioselective Organocatalytic Friedel-Crafts Alkylations, Curr. Org. Chem. 2011, 15, 4022-4045. (Invited Review)
8. Zhang, F.-G.; Yang, Q.-Q.; Xuan, J.; Lu, H.-H.; Duan, S.-W.; Chen, J.-R.; Xiao, W.-J.* Enantioselective Conjugate Addition of Oximes to Trisubstituted β-Nitroacrylates: An Organocatalytic Approach to β2,2-Amino Acid Derivatives, Org. Lett. 2010, 12, 5636–5639.
7. Lu, H.-H.; Liu, H.; Wu, W.; Wang, X.-F.; Lu, L.-Q.; Xiao, W.-J.* Catalytic Asymmetric Intramolecular Hydroarylations of ω-Aryloxy- and Arylamino Tethered α,β-Unsaturated Aldehydes, Chem. Eur. J. 2009, 15, 2742-2746.
6. Lu, H.-H.; Meng, X.-G.; Zhang, F.-G.; Duan, S.-W.; Xiao, W.-J.* Enantioselective Michael Reactions of β,β-Disubstituted Nitroalkenes: A New Approach to β2,2-Amino Acids with Hetero-Quaternary Stereocenters, Org. Lett. 2009, 11, 3946-3949.
5. Lu, H.-H.; Wang, X.-F.; Yao, C.-J.; Zhang, J.-M.; Wu, H.; Xiao, W.-J.* Highly Enantioselective Organocatalytic Michael Addition of Nitroalkanes to 4-oxo-Enoates, Chem. Commun. 2009, 4251-4253.
4. Chen, J.-R.; Lai, Y.-Y.; Lu, H.-H.; Wang, X.-F.; Xiao, W.-J.* Highly Enantioselective Desymmetrization of meso- and Prochiral Cyclic Ketones via Organocatalytic Michael Reaction, Tetrahedron 2009, 65, 9238-9243.
3. Dong, H.-M.; Lu, H.-H.; Lu, L.-Q.; Chen, C.-B.; Xiao, W.-J.* Asymmetric Friedel-Crafts Alkylations of Indoles with Ethyl Glyoxylate Catalyzed by (S)-BINOL-Ti (IV) Complex: Direct Access to Enantiomerically Enriched 3-Indolyl-hydroxyacetates, Adv. Synth. Catal. 2007, 349, 1597-1603.
2. Cao, Y.-J.; Lu, H.-H.; Lai, Y.-Y.; Lu, L.-Q.; Xiao, W.-J.* An Effective Bifunctional Thiourea Catalyst for Highly Enantio- and Diastereoselective Michael Addition of Cyclohexanone to Nitroolefins, Synthesis 2006, 3795-3800.
1. Chen, J.-R.; Lu, H.-H.; Li, X.-Y.; Cheng, L.; Wan, J.; Xiao, W.-J.* Readily Tunable and Bifunctional L-Prolinamide Derivatives: Design and Application in the Direct Enantioselective Aldol Reactions, Org. Lett. 2005, 7, 4543-4545.
