Vicinal carbon stereocenters constructed with excellent selectivities (up to 99% ee, >99:1 dr)
Penta-coordinated silicates are crucial intermediates
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
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.
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.
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