Catalytic regio- and stereoselective intermolecular [5+2] cycloaddition via conjugative activation of oxidopyrylium.

A catalytic stereodivergent intermolecular [5+2] cycloaddition of maltol-type oxidopyrylium through conjugative activation was reported, which featured high stereoselectivity, good compatibility and mild conditions, providing a convenient access route to various seven-membered heterocycles in moderate to excellent yields. In addition, a discrete mechanism was proposed to illustrate the stereoselectivity.

[1]  Xin Liu,et al.  Total Synthesis of Natural Products with Bridged Bicyclo[m.n.1] Ring Systems via Type II [5 + 2] Cycloaddition. , 2020, Accounts of chemical research.

[2]  Huanfeng Jiang,et al.  Deconstructive Reorganization: De Novo Synthesis of Hydroxylated Benzofuran. , 2020, Angewandte Chemie.

[3]  Xiaohong Lin,et al.  Asymmetric Total Synthesis of (-)-Vinigrol. , 2019, Journal of the American Chemical Society.

[4]  Junyang Liu,et al.  Asymmetric Total Synthesis of Cerorubenic Acid-III. , 2019, Journal of the American Chemical Society.

[5]  Shifa Zhu,et al.  Mechanism-Guided Scaffold Diversification: Perturbing and Trapping the Intermediates of Maltol-Type Cascade Claisen Rearrangement. , 2018, Organic letters.

[6]  Weiping Tang,et al.  Intermolecular Regio- and Stereoselective Hetero-[5+2] Cycloaddition of Oxidopyrylium Ylides and Cyclic Imines. , 2018, Angewandte Chemie.

[7]  Shifa Zhu,et al.  Cascade Claisen Rearrangement: Rapid Synthesis of Polysubstituted Salicylaldehydes and Total Syntheses of Hemigossypol and Gossypol. , 2018, Angewandte Chemie.

[8]  M. Shimizu,et al.  Triethylamine Enables Catalytic Generation of Oxidopyrylium Ylides for [5+2] Cycloadditions with Alkenes: An Efficient Entry to 8‐Oxabicyclo[3.2.1]octane Frameworks , 2018 .

[9]  Kai Chen,et al.  Transition-Metal-Catalyzed Intramolecular Nucleophilic Addition of Carbonyl Groups to Alkynes , 2018, Chem.

[10]  L. Bejcek,et al.  Oxidopyrylium [5+2] Cycloaddition Chemistry: Historical Perspective and Recent Advances (2008-2018). , 2018, Tetrahedron.

[11]  Junyang Liu,et al.  Asymmetric Total Synthesis of Cyclocitrinol. , 2018, Journal of the American Chemical Society.

[12]  J. Zhao,et al.  Recent synthetic studies towards natural products via [5 + 2] cycloaddition reactions , 2018 .

[13]  M. Shimizu,et al.  Efficient generation of an oxidopyrylium ylide using a Pd catalyst and its [5+2] cycloadditions with several dipolarophiles. , 2018, Chemical communications.

[14]  S. E. Brenner-Moyer,et al.  Catalytic Enantioselective Intermolecular [5 + 2] Dipolar Cycloadditions of a 3-Hydroxy-4-pyrone-Derived Oxidopyrylium Ylide. , 2017, Organic letters.

[15]  M. Shi,et al.  Lu's [3 + 2] cycloaddition of allenes with electrophiles: discovery, development and synthetic application , 2017 .

[16]  Michael P. D'Erasmo,et al.  Discovery and Development of a Three-Component Oxidopyrylium [5 + 2] Cycloaddition. , 2016, The Journal of organic chemistry.

[17]  J. Vicario,et al.  Mechanistic Insights into the Mode of Action of Bifunctional Pyrrolidine-Squaramide-Derived Organocatalysts. , 2016, Chemistry.

[18]  M. K. Brown,et al.  Cyclobutane and cyclobutene synthesis: catalytic enantioselective [2+2] cycloadditions. , 2015, Angewandte Chemie.

[19]  T. Hashimoto,et al.  Recent advances of catalytic asymmetric 1,3-dipolar cycloadditions. , 2015, Chemical reviews.

[20]  J. Vicario,et al.  Catalytic enantioselective [5+2] cycloaddition between oxidopyrylium ylides and enals under dienamine activation. , 2015, Angewandte Chemie.

[21]  Wei Chen,et al.  Dearomative indole [5+2] cycloaddition reactions: stereoselective synthesis of highly functionalized cyclohepta[b]indoles. , 2014, Angewandte Chemie.

[22]  John R. Goodell,et al.  Investigation of oxidopyrylium-alkene [5+2] cycloaddition conjugate addition cascade (C3) sequences. , 2014, Chemical communications.

[23]  E. Jacobsen,et al.  Catalytic asymmetric synthesis of 8-oxabicyclooctanes by intermolecular [5+2] pyrylium cycloadditions. , 2014, Angewandte Chemie.

[24]  M. Zhang,et al.  Stereoselective total synthesis of hainanolidol and harringtonolide via oxidopyrylium-based [5 + 2] cycloaddition. , 2013, Journal of the American Chemical Society.

[25]  J. Stryker,et al.  [5 + 2] cycloaddition reactions in organic and natural product synthesis. , 2013, Chemical reviews.

[26]  S. Thirumalairajan,et al.  Synthesis of optically active seven-membered 1,5-anhydrocarbasugars and 1,4,5-tribenzoyloxy-2-ethoxy cycloheptanes via [5+2] cycloaddition , 2012 .

[27]  G. Hammond,et al.  Ligand effects and ligand design in homogeneous gold(I) catalysis. , 2012, Journal of the American Chemical Society.

[28]  E. Jacobsen,et al.  Dual catalysis in enantioselective oxidopyrylium-based [5 + 2] cycloadditions. , 2011, Journal of the American Chemical Society.

[29]  P. Wender,et al.  A Gateway Synthesis, PKC Affinities and Cell Growth Activities of Daphnane Congeners , 2011, Nature chemistry.

[30]  M. Salunkhe,et al.  Reductive Studies on 3-Oxidopyrylium-alkene [5 + 2] Cycloadducts: Access to Some Hydroxy Cycloheptenoids , 2011 .

[31]  K. Nicolaou,et al.  Total synthesis of englerin A. , 2010, Journal of the American Chemical Society.

[32]  Vishwakarma Singh,et al.  Cycloaddition of Oxidopyrylium Species in Organic Synthesis , 2008 .

[33]  M. Harmata.  Asymmetric Catalytic [4+3] Cycloaddition Reactions , 2006 .

[34]  Bencan Tang,et al.  A biomimetic total synthesis of (+)-intricarene , 2006 .

[35]  Dirk Trauner,et al.  Expedient synthesis of (+/-)-bipinnatin J. , 2006, Organic letters.

[36]  J. Mascareñas,et al.  A sulfinyl-directed asymmetric [5C + 2C] intramolecular acetoxypyranone-alkene cycloaddition. , 2002, Organic letters.

[37]  N. Ohmori.  Synthetic study of phomoidride B (CP-263,114); utilization of the oxidopyrylium [5 + 2] cycloaddition. , 2001, Chemical communications.

[38]  M. Schnute,et al.  The First Formal Asymmetric Synthesis of Phorbol , 1997 .

[39]  P. Wender,et al.  Studies on tumor promoters. 11. A new [5+2] cycloaddition method and its application to the synthesis of BC ring precursors of phorboids , 1991 .

[40]  P. G. Sammes,et al.  The preparation and some reactions of 3-oxidopyrylium , 1983 .

[41]  R. Vicente,et al.  Zinc-Mediated Synthesis of Heterocycles , 2018 .

[42]  Atsushi Arakaki,et al.  Organic & Biomolecular Chemistry , 2015 .