Divergent synthesis of hydropyridine derivatives via nitrogen-containing Lewis base mediated regioselective [4 + 2] cyclizations

A nitrogen-containing Lewis base mediated regioselective [4 + 2] cyclization strategy between allenic esters and α,β-unsaturated ketimines was discovered, affording a series of hydropyridine derivatives in moderate to good yields under mild conditions.

[1]  Sang‐gi Lee,et al.  Transition metal-catalyzed site- and regio-divergent C-H bond functionalization. , 2017, Chemical Society reviews.

[2]  Xingwei Li,et al.  Catalyst-Controlled Regiodivergent Alkyne Insertion in the Context of C-H Activation and Diels-Alder Reactions: Synthesis of Fused and Bridged Cycles. , 2017, Angewandte Chemie.

[3]  Pan‐Lin Shao,et al.  Enantioselective Synthesis of Tetrahydropyridines/Piperidines via Stepwise [4 + 2]/[2 + 2] Cyclizations. , 2017, Organic letters.

[4]  Ying‐Chun Chen,et al.  Switchable divergent asymmetric synthesis via organocatalysis. , 2017, Chemical Society reviews.

[5]  Yun He,et al.  Selective Aza Diels-Alder and Domino [4+2]/[2+2] Cycloaddition Reactions of Arynes with N-Sulfonyl Ketimines. , 2017, The Journal of organic chemistry.

[6]  Hequan Yao,et al.  Catalyst‐Controlled Regiodivergent Dehydrogenative Heck Reaction of 4‐Arylthiophene/Furan‐3‐Carboxylates , 2016 .

[7]  Leijie Zhou,et al.  Phosphine-Catalyzed Enantioselective [4 + 3] Annulation of Allenoates with C,N-Cyclic Azomethine Imines: Synthesis of Quinazoline-Based Tricyclic Heterocycles. , 2016, Organic letters.

[8]  J. Baltaze,et al.  Organocatalyzed [4+2] Annulation of All-Carbon Tetrasubstituted Alkenes with Allenoates: Synthesis of Highly Functionalized 2H- and 4H-Pyran Derivatives. , 2016 .

[9]  Penghao Jia,et al.  Bifunctional-Phosphine-Catalyzed Sequential Annulations of Allenoates and Ketimines: Construction of Functionalized Poly-heterocycle Rings. , 2016, Angewandte Chemie.

[10]  S. Ye,et al.  Enantioselective N-heterocyclic carbene-catalyzed synthesis of saccharine-derived dihydropyridinones with cis-selectivity. , 2016, Organic & biomolecular chemistry.

[11]  Yixin Lu,et al.  Amino Acid-Derived Bifunctional Phosphines for Enantioselective Transformations. , 2016, Accounts of chemical research.

[12]  Yixin Lu,et al.  Phosphine-mediated Highly Enantioselective Spirocyclization with Ketimines as Substrates. , 2016, Angewandte Chemie.

[13]  M. A. Pericàs,et al.  A Recyclable, Immobilized Analogue of Benzotetramisole for Catalytic Enantioselective Domino Michael Addition/Cyclization Reactions in Batch and Flow , 2016 .

[14]  Srinivas Thadkapally,et al.  Catalyst-controlled divergence in cycloisomerisation reactions of N-propargyl-N-vinyl sulfonamides: gold-catalysed synthesis of 2-sulfonylmethyl pyrroles and dihydropyridines. , 2015, Chemical communications.

[15]  Hajime Ito,et al.  Catalyst-controlled regiodivergent C-H borylation of multifunctionalized heteroarenes by using iridium complexes. , 2015, Chemistry.

[16]  Lei Wang,et al.  DMAP-Catalyzed [2 + 4] Cycloadditions of Allenoates with N-Acyldiazenes: Direct Method to 1,3,4-Oxadiazine Derivatives. , 2015, Organic letters.

[17]  K. Swamy,et al.  Divergence in the reactivity between amine- and phosphine-catalyzed cycloaddition reactions of allenoates with enynals: one-pot gold-catalyzed synthesis of trisubstituted benzofurans from the [3 + 2] cycloadduct via 1,2-alkyl migration and dehydrogenation. , 2015, The Journal of organic chemistry.

[18]  Meijia Chang,et al.  Divergent Phosphine-Catalyzed [2+4] or [3+2] Cycloaddition Reactions of γ-Substituted Allenoates with Oxadienes , 2015 .

[19]  Yixin Lu,et al.  Highly enantioselective synthesis of 3,4-dihydropyrans through a phosphine-catalyzed [4+2] annulation of allenones and β,γ-unsaturated α-keto esters. , 2015, Journal of the American Chemical Society.

[20]  Xin Li,et al.  Highly enantioselective [4 + 2] cycloaddition of allenoates and 2-olefinic benzofuran-3-ones. , 2015, Organic letters.

[21]  J. Gu,et al.  β,γ-Regioselective inverse-electron-demand aza-Diels-Alder reactions with α,β-unsaturated aldehydes via dienamine catalysis. , 2014, Organic letters.

[22]  O. Kwon,et al.  Phosphine catalysis of allenes with electrophiles. , 2014, Chemical Society reviews.

[23]  B. Bhat,et al.  Metal free stereoselective synthesis of functionalized enamides. , 2014, Organic & biomolecular chemistry.

[24]  O. Kwon,et al.  Advances in nucleophilic phosphine catalysis of alkenes, allenes, alkynes, and MBHADs. , 2013, Chemical communications.

[25]  Jing Gu,et al.  1-Azadienes as regio- and chemoselective dienophiles in aminocatalytic asymmetric Diels-Alder reaction. , 2013, Organic letters.

[26]  Zhengming Li,et al.  Phosphine-catalyzed domino reaction: an efficient method for the synthesis of bicyclo[3.2.0]heptenes skeleton. , 2013, Organic letters.

[27]  Jun Li,et al.  Highly diastereoselective DABCO-catalyzed [3 + 3]-cycloaddition of 1,4-dithiane-2,5-diol with azomethine imines. , 2013, Organic letters.

[28]  Y. Huang,et al.  One step synthesis of benzoxazepine derivatives via a PPh(3) catalyzed aza-MBH domino reaction between salicyl N-tosylimines and allenoates. , 2013, Chemical communications.

[29]  Y. Huang,et al.  Domino Cyclization Initiated by Cross‐Rauhut–Currier Reactions , 2013 .

[30]  Zhengming Li,et al.  Phosphine-catalyzed domino benzannulation: an efficient method to construct biaryl skeletons. , 2013, Organic letters.

[31]  Yan Zhao,et al.  Phosphine-catalyzed [3 + 2] cycloaddition of sulfamate-derived cyclic imines with allenoate: synthesis of sulfamate-fused dihydropyrroles. , 2013, The Journal of organic chemistry.

[32]  T. Loh,et al.  Organocatalytic synthesis of highly functionalized pyridines at room temperature. , 2013, Angewandte Chemie.

[33]  H. W. Lam,et al.  Catalyst-controlled divergent C-H functionalization of unsymmetrical 2-aryl cyclic 1,3-dicarbonyl compounds with alkynes and alkenes. , 2013, Journal of the American Chemical Society.

[34]  M. Shi,et al.  Recent advances in organocatalytic asymmetric Morita-Baylis-Hillman/aza-Morita-Baylis-Hillman reactions. , 2013, Chemical reviews.

[35]  Y. Huang,et al.  Tuning catalysts to tune the products: phosphine-catalyzed aza-Michael addition reaction of hydrazones with allenoates. , 2013, Chemistry, an Asian journal.

[36]  Ying Wang,et al.  DABCO and Bu3P catalyzed [4 + 2] and [3 + 2] cycloadditions of 3-acyl-2H-chromen-ones and ethyl 2,3-butadienoate. , 2012, Organic & biomolecular chemistry.

[37]  Ying‐Chun Chen,et al.  Asymmetric aza‐Diels–Alder and Cation–olefin Cyclization Sequence: a Concise Way to Fused Chiral Cyclopenta[b]piperidines , 2012 .

[38]  Hui Liu,et al.  Amine-catalyzed formal (3 + 3) annulations of 2-(acetoxymethyl)buta-2,3-dienoate with sulfur ylides: synthesis of 4H-pyrans bearing a vinyl sulfide group. , 2012, Chemical communications.

[39]  B. Borhan,et al.  Development of a formal catalytic asymmetric [4+2] addition of ethyl-2,3-butadienoate with acyclic enones. , 2011, Organic letters.

[40]  E. Corsini,et al.  Design, synthesis and biological evaluation of novel desmuramyldipeptide analogs. , 2011, European journal of medicinal chemistry.

[41]  W. Goddard,et al.  Phosphine-catalyzed annulations of azomethine imines: allene-dependent [3 + 2], [3 + 3], [4 + 3], and [3 + 2 + 3] pathways. , 2011, Journal of the American Chemical Society.

[42]  Xiaofeng Tong,et al.  Enantioselective amine-catalyzed [4+2] annulations of allenoates and oxo-dienes: an asymmetric synthesis of dihydropyrans. , 2011, Angewandte Chemie.

[43]  M. Shi,et al.  Phosphine- and nitrogen-containing Lewis base catalyzed highly regioselective and geometric selective cyclization of isatin derived electron-deficient alkenes with ethyl 2,3-butadienoate. , 2011, Organic letters.

[44]  Zhi‐Xiang Wang,et al.  Unusual formal [4 + 2] cycloaddition of ethyl allenoate with arylidenoxindoles: synthesis of dihydropyran-fused indoles. , 2011, Organic letters.

[45]  Xiaofeng Tong,et al.  Amine-catalyzed (3+n) annulations of 2-(acetoxymethyl)buta-2,3-dienoates with 1,n-bisnucleophiles (n = 3-5). , 2010, Chemical communications.

[46]  A. Marinetti,et al.  Enantioselective Phosphine Organocatalysis , 2010 .

[47]  Scott J. Miller,et al.  Enantioselective catalysis and complexity generation from allenoates. , 2009, Chemical Society reviews.

[48]  K. Jiang,et al.  Organocatalytic regio- and stereoselective inverse-electron-demand aza-Diels-Alder reaction of alpha,beta-unsaturated aldehydes and N-tosyl-1-aza-1,3-butadienes. , 2009, Angewandte Chemie.

[49]  Weiping Tang,et al.  DABCO-catalyzed 1,4-bromolactonization of conjugated enynes: highly stereoselective formation of a stereogenic center and an axially chiral allene. , 2009, Journal of the American Chemical Society.

[50]  Y. Huang,et al.  PPh3-catalyzed domino reaction: a facile method for the synthesis of chroman derivatives. , 2009, Organic letters.

[51]  C. Cai,et al.  Organic Base Catalyzed Carbonyl Allylation of Methyl Trifluoropyruvate with Activated Alkenes , 2009 .

[52]  You Huang,et al.  Bifunctional phosphine-catalyzed domino reaction: highly stereoselective synthesis of cis-2,3-dihydrobenzofurans from salicyl N-thiophosphinyl imines and allenes. , 2009, Organic letters.

[53]  Jian Zhou,et al.  Phosphine-triggered synthesis of functionalized cyclic compounds. , 2008, Chemical Society reviews.

[54]  S. Denmark,et al.  Lewis base catalysis in organic synthesis. , 2008, Angewandte Chemie.

[55]  H. Nemoto,et al.  Three-component coupling reaction and cyclization of N-tosylimines and TMS-substituted propiolate mediated by DABCO. , 2008, The Journal of organic chemistry.

[56]  S. Mukherjee,et al.  Asymmetric enamine catalysis. , 2007, Chemical reviews.

[57]  R. Menon,et al.  Engaging zwitterions in carbon-carbon and carbon-nitrogen bond-forming reactions: A promising synthetic strategy. , 2006, Accounts of chemical research.

[58]  Mingjin Fan,et al.  DABCO-catalyzed reaction of alpha-halo carbonyl compounds with dimethyl acetylenedicarboxylate: a novel method for the preparation of polysubstituted furans and highly functionalized 2H-pyrans. , 2005, The Journal of organic chemistry.

[59]  R. Tubino,et al.  New pi-extended water-soluble squaraines as singlet oxygen generators. , 2005, Organic letters.

[60]  Shengming Ma,et al.  Some typical advances in the synthetic applications of allenes. , 2005, Chemical reviews.

[61]  M. Shi,et al.  DABCO-catalyzed reaction of allenic esters and ketones with salicyl N-tosylimines: synthesis of highly functionalized chromenes. , 2005, Organic letters.

[62]  W. Roush,et al.  Nucleophilic Phosphine Organocatalysis , 2004 .

[63]  O. Kwon,et al.  An expedient phosphine-catalyzed [4 + 2] annulation: synthesis of highly functionalized tetrahydropyridines. , 2003, Journal of the American Chemical Society.

[64]  D. Basavaiah,et al.  Recent advances in the Baylis-Hillman reaction and applications. , 2003, Chemical reviews.

[65]  M. Ortega,et al.  Haouamines A and B: a new class of alkaloids from the ascidian Aplidium haouarianum. , 2003, The Journal of organic chemistry.

[66]  X. Lu,et al.  Reactions of electron-deficient alkynes and allenes under phosphine catalysis. , 2001, Accounts of chemical research.

[67]  G. C. Fu Enantioselective nucleophilic catalysis with "Planar-Chiral" heterocycles. , 2000, Accounts of chemical research.

[68]  K. Jacobson,et al.  Interaction of 1,4-dihydropyridine and pyridine derivatives with adenosine receptors: selectivity for A3 receptors. , 1996, Journal of medicinal chemistry.

[69]  D. Triggle,et al.  Dimeric 1,4-dihydropyridines as calcium channel antagonists. , 1988, Journal of medicinal chemistry.

[70]  W. Maier,et al.  Selective cleavage of carbon-nitrogen bonds with platinum , 1984 .

[71]  J. Carson,et al.  Alkali and Alkaline Earth Metals as Catalysts in the Hydrogenation of Organic Compounds , 1941 .