Amine-N-heterocyclic carbene cascade catalysis for the asymmetric synthesis of fused indane derivatives with multiple chiral centres.

An aminocatalytic asymmetric Diels-Alder reaction of 2,4-dienals and labile 1-indenones in situ generated from 3-bromo-1-indanones was developed, producing highly fused indane products with multiple chiral centres followed by a cascade N-heterocyclic carbene-mediated benzoin condensation.

[1]  K. Jørgensen,et al.  Aminocatalytic remote functionalization strategies , 2013 .

[2]  Jinxing Ye,et al.  Aminocatalyzed asymmetric Diels-Alder reaction of 2,4-dienals and rhodanine/hydantoin derivatives. , 2013, Chemical communications.

[3]  K. Houk,et al.  Zwitterions and unobserved intermediates in organocatalytic Diels-Alder reactions of linear and cross-conjugated trienamines. , 2013, Journal of the American Chemical Society.

[4]  Ying‐Chun Chen,et al.  Aminocatalytic asymmetric exo-Diels-Alder reaction with methiodide salts of Mannich bases and 2,4-dienals to construct chiral spirocycles. , 2013, Organic letters.

[5]  Ying‐Chun Chen,et al.  A concise assembly of electron-deficient 2,4-dienes and 2,4-dienals: regio- and stereoselective exo-Diels-Alder and redox reactions through sequential amine and carbene catalysis. , 2013, Angewandte Chemie.

[6]  Indresh Kumar,et al.  Asymmetric trienamine catalysis: new opportunities in amine catalysis. , 2013, Organic & biomolecular chemistry.

[7]  K. Jørgensen,et al.  Enantioselective H-bond-directing approach for trienamine-mediated reactions in asymmetric synthesis. , 2012, Angewandte Chemie.

[8]  Rebecca L. Davis,et al.  Cross-trienamines in Asymmetric Organocatalysis , 2012, Journal of the American Chemical Society.

[9]  Peter R. Schreiner,et al.  Evolution of asymmetric organocatalysis: multi- and retrocatalysis , 2012 .

[10]  Ying‐Chun Chen,et al.  Aminocatalytic asymmetric Diels-Alder reactions via HOMO activation. , 2012, Accounts of chemical research.

[11]  P. Melchiorre,et al.  Extending the aminocatalytic HOMO-raising activation strategy: where is the limit? , 2012, Angewandte Chemie.

[12]  D. Trauner,et al.  A total synthesis prompts the structure revision of haouamine B. , 2012, Journal of the American Chemical Society.

[13]  J. Gu,et al.  Trienamine catalysis with 2,4-dienones: development and application in asymmetric Diels-Alder reactions. , 2012, Angewandte Chemie.

[14]  Pu-Sheng Wang,et al.  Hybrid metal/organo relay catalysis enables enynes to be latent dienes for asymmetric Diels-Alder reaction. , 2012, Journal of the American Chemical Society.

[15]  K. Scheidt,et al.  Cooperative Lewis acid/N-heterocyclic carbene catalysis. , 2012, Chemical science.

[16]  K. Jørgensen,et al.  The diarylprolinol silyl ether system: a general organocatalyst. , 2012, Accounts of chemical research.

[17]  Eduardo C. Escudero‐Adán,et al.  Multicatalytic asymmetric synthesis of complex tetrahydrocarbazoles via a Diels-Alder/benzoin reaction sequence. , 2012, Organic letters.

[18]  D. MacMillan,et al.  Synergistic Catalysis: A Powerful Synthetic Strategy for New Reaction Development. , 2012, Chemical science.

[19]  J. Yue,et al.  Walsucochinoids A and B: new rearranged limonoids from Walsura cochinchinensis. , 2012, Organic letters.

[20]  N. T. Patil,et al.  A one-pot catalysis: the strategic classification with some recent examples. , 2012, Organic & biomolecular chemistry.

[21]  D. Enders,et al.  N-heterocyclic carbene catalyzed domino reactions. , 2012, Angewandte Chemie.

[22]  Ying‐Chun Chen,et al.  exo-Selective asymmetric Diels-Alder reaction of 2,4-dienals and nitroalkenes by trienamine catalysis. , 2011, Angewandte Chemie.

[23]  P. Melchiorre,et al.  Asymmetric catalysis of Diels-Alder reactions with in situ generated heterocyclic ortho-quinodimethanes. , 2011, Journal of the American Chemical Society.

[24]  C. Jacobsen,et al.  Organocatalytic iminium ion/carbene reaction cascade for the formation of optically active 2,4-disubstituted cyclopentenones. , 2011, Organic letters.

[25]  K. Jørgensen,et al.  Asymmetric trienamine catalysis for the construction of structurally rigid cyclic α,α-disubstituted amino acid derivatives. , 2011, Chemistry.

[26]  T. Rovis,et al.  Enamine/Carbene Cascade Catalysis in the Diastereo- and Enantioselective Synthesis of Functionalized Cyclopentanones. , 2011, Chemical science.

[27]  D. Enders,et al.  Dual Secondary Amine/N‐Heterocyclic Carbene Catalysis in the Asymmetric Michael/Cross‐Benzoin Cascade Reaction of β‐Oxo Sulfones with Enals , 2011 .

[28]  G. Mehta,et al.  A de novo Diels–Alder strategy toward the novel pentacyclic natural product fluostatin C: a concise synthesis of 6-deoxyfluostatin C , 2011 .

[29]  K. Jørgensen,et al.  Trienamines in asymmetric organocatalysis: Diels-Alder and tandem reactions. , 2011, Journal of the American Chemical Society.

[30]  A. Alexakis,et al.  Access to high levels of molecular complexity by one-pot iridium/enamine asymmetric catalysis. , 2011, Angewandte Chemie.

[31]  Gene-Hsiang Lee,et al.  Dynamic kinetic asymmetric synthesis of five contiguous stereogenic centers by sequential organocatalytic stetter and Michael-aldol reaction: enantioselective synthesis of fully substituted cyclopentanols bearing a quaternary stereocenter. , 2011, Organic letters.

[32]  B. Trost,et al.  Contemporaneous dual catalysis by coupling highly transient nucleophilic and electrophilic intermediates generated in situ. , 2011, Journal of the American Chemical Society.

[33]  T. Lambert,et al.  Multicatalysis: Advancing Synthetic Efficiency and Inspiring Discovery , 2010 .

[34]  S. You,et al.  Enantioselective intramolecular aza-Michael additions of indoles catalyzed by chiral phosphoric acids. , 2010, Angewandte Chemie.

[35]  B. Hong,et al.  Sequential organocatalytic Stetter and Michael-Aldol condensation reaction: asymmetric synthesis of fully substituted cyclopentenes via a [1 + 2 + 2] annulation strategy. , 2010, Organic letters.

[36]  K. Jørgensen,et al.  Organocatalytic preparation of simple β-hydroxy and β-amino esters: low catalyst loadings and gram-scale synthesis. , 2010, Organic letters.

[37]  K. Scheidt,et al.  Cooperative Catalysis by Carbenes and Lewis Acids in a Highly Stereoselective Route to γ-Lactams , 2010, Nature Chemistry.

[38]  A. Mazzanti,et al.  Asymmetric catalytic aziridination of cyclic enones. , 2010, Chemistry, an Asian journal.

[39]  Xiaodong Shi,et al.  When Organocatalysis Meets Transition‐Metal Catalysis , 2010 .

[40]  D. Dixon,et al.  Multiple-organocatalyst-promoted cascade reaction: a fast and efficient entry into fully substituted piperidines. , 2010, Chemistry.

[41]  Jian Zhou.  Recent advances in multicatalyst promoted asymmetric tandem reactions. , 2010, Chemistry, an Asian journal.

[42]  D. Enders,et al.  Organocatalytic cascade reactions as a new tool in total synthesis. , 2010, Nature chemistry.

[43]  T. Rovis,et al.  Asymmetric synthesis of functionalized cyclopentanones via a multicatalytic secondary amine/N-heterocyclic carbene catalyzed cascade sequence. , 2009, Journal of the American Chemical Society.

[44]  C. Vila,et al.  Trends in organocatalytic conjugate addition to enones: an efficient approach to optically active alkynyl, alkenyl, and ketone products. , 2009, Angewandte Chemie.

[45]  Phil S. Baran,et al.  Scalable total synthesis and biological evaluation of haouamine A and its atropisomer. , 2009, Journal of the American Chemical Society.

[46]  L. Gong,et al.  Consecutive intramolecular hydroamination/asymmetric transfer hydrogenation under relay catalysis of an achiral gold complex/chiral Brønsted acid binary system. , 2009, Journal of the American Chemical Society.

[47]  D. MacMillan,et al.  Cycle-specific organocascade catalysis: application to olefin hydroamination, hydro-oxidation, and amino-oxidation, and to natural product synthesis. , 2009, Angewandte Chemie.

[48]  D. MacMillan,et al.  The advent and development of organocatalysis , 2008, Nature.

[49]  N. Uchiyama,et al.  Steric tuning of silylacetylenes and chiral phosphine ligands for rhodium-catalyzed asymmetric conjugate alkynylation of enones. , 2008, Journal of the American Chemical Society.

[50]  A. Tramontano,et al.  A structure-guided approach to an orthogonal estrogen-receptor-based gene switch activated by ligands suitable for in vivo studies. , 2006, Journal of medicinal chemistry.

[51]  R. Süssmuth,et al.  The Structures of Fluostatins C, D and E, Novel Members of the Fluostatin Family , 2006, The Journal of Antibiotics.

[52]  Yong Huang,et al.  Enantioselective organo-cascade catalysis. , 2005, Journal of the American Chemical Society.

[53]  S. Matsunaga,et al.  Direct catalytic asymmetric Michael reaction of hydroxyketones: asymmetric Zn catalysis with a Et2Zn/linked-BINOL complex. , 2003, Journal of the American Chemical Society.

[54]  H. W. Scheeren,et al.  High pressure and thermal Diels–Alder reaction of 2-vinyl-benzo[b]furan and 2-vinyl-benzo[b]thiophene. Synthesis of new condensed heterocycles , 2001 .

[55]  A. Marrocchi,et al.  Diels-Alder reactions of arylethenes. Synthesis of some [5]phenacenes and fluorenoanthracenes , 1998 .

[56]  A. Marrocchi,et al.  High Pressure Diels-Alder Reactions of 2-Vinyl-3,4-Dihydronaphthalene. Synthesis of Cyclopenta[c]- and Indeno[c]Phenanthrenones. , 1995 .

[57]  A. Coop,et al.  Ring constrained analogues of the thevinones; Diels-Alder reactions of thebaines with 1-indenone and methylene cycloalkanones , 1995 .

[58]  H. Szmant,et al.  Thiol-olefin cooxidation reaction. 6. A new convenient route to 1-substituted indenes. Indenone as dienophile in Diels-Alder reactions , 1978 .

[59]  H. O. House,et al.  Perhydroindan derivatives. 18. The use of indenone ketals as dienophiles , 1977 .

[60]  E. Campaigne,et al.  Preparation of an .alpha.-unsubstituted 1-indenone and its dimer , 1968 .