Nitroalkene and Related Cycloaddition (Including Tandem)

[306] Tandem Double Intramolecular [4+2]/[3+2] Cycloadditions of Nitroalkenes: Construction of the Pentacyclic Core Structure of Daphnilactone B (with R. Y. Baiazitov and S. T. Nguyen) Tetrahedron 2009, 65, 6535-6548.

[295] Asymmetric Synthesis of the ABCD Ring System of Daphnilactone B via a Tandem, Double Intramolecular [4+2]/[3+2] Cycloaddition Strategy (with R. Y. Baiazitov and S. Nguyen) Heterocycles (Dedicated Issue to Ryoji Noyori) 2008, 76, 143-154.

[276] Lewis Acid-Promoted Conjugate Addition of Dienol Silyl Ethers to Nitroalkenes: Synthesis of 3-Substituted Azepanes (with M. Xie) J. Org. Chem. 2007, 72, 7050-7053.

[268] A Tandem Nitroalkene Conjugate Addition/[3+2] Cycloaddition Approach to the Synthesis of the Pentacyclic Core of (±)-Scandine (with J. J. Cottell) Adv. Synth. Cat. 2006, 348, 2397-2402.

[264] Synthesis, X-Ray Crystallography and Computational Analysis of 1-Azafenestranes (with J. I. Montgomery and L. A. Kramps) J. Am. Chem. Soc. 2006, 128, 11620-11630.

[263] A General Synthesis of N-Vinyl Nitrones (with J. I. Montgomery) J. Org. Chem. 2006, 71, 6211-6220.

[253] Tandem Double-Intramolecular [4+2]/[3+2] Cycloadditons of Nitroalkenes. Studies toward a Total Synthesis of Daphnilactone B: Piperidine Ring Construction (with R. Y. Baiazitov) J. Org. Chem. 2006, 71, 593-605.

[248] Intramolecular [4+2] Cycloaddition of Nitroalkenes for Construction of Vicinal Quarternary Stereocenters (with R. Baiazitov) Org. Lett. 2005, 7, 5617-5620.

[242] Synthesis of cis,cis,cis,cis-[5.5.5.4]-1-Azafenestrane with Discovery of an Unexpected Dyotropic Rearrangement (with J. I. Montgomery) Angew. Chem. Int. Ed. 2005, 44, 3732-3736.

[226] 2-Silyloxy-1,2-oxazines, a New Type of Acetals of Conjugated Nitroso Alkenes (with A. A. Tishkov, A. V. Lesiv, Y. A. Khomutova, Y. A. Strelenko, I. D. Nesterov, M. Y. Antipin, Ioffe, S. A.) J. Org. Chem. 2003, 68, 9477-9480.

[223] Tandem Double Intramolecular [4+2]/[3+2] Cycloadditions of Nitroalkenes. The Fused/Bridged Mode (with L. Gomez) J. Org. Chem. 2003, 68, 8015-8024.

[210] Tandem Inter [4+2]/Intra [3+2] Cycloadditions of Nitroalkenes. Application to the Synthesis of Aminocarbasugars (with M. Juhl) Helv. Chim. Acta 2002, 85, 3712-3736.

[208] Inter- and Intramolecular [4+2] Cycloaddition of Nitroalkenes with Allenylsilanes. A Case of Unexpected Regioselectivity (with L. Gomez) Heterocycles 2002, 58, 129-136.

[204] Synthesis of cis,cis,cis,cis-[5.5.5.5]-1-Azafenestrane (with L. H. Kramps and J. I. Montgomery) Angew. Chem. Int. Ed. 2002, 41, 4122-4125.

[193] Studies on the Reduction and Hydrolysis of Nitroso Acetals (with V. Guagnano and J. Vaugeois) Can. J. Chem. 2001, 79, 1606-1616.

[190] Tandem Double Intramolecular [4+2]/[3+2] Cycloadditions of Nitroalkenes (with L. Gomez) Org. Lett. 2001, 3, 2907-2910.

[184] Synthesis of (+)-1-Epiaustraline (with J. J. Cottell) J. Org. Chem. 2001, 66, 4276-4284.

[170] Synthesis of (–)-7-Epiaustraline and (–)-1-Epicastanospermine (with B. Herbert) J. Org. Chem. 2000, 65, 2887-2896.

[169] Synthesis of (+)-Casuarine (with A. R. Hurd) J. Org. Chem. 2000, 65, 2875-2886.

[166] Synthesis of (+)-Casuarine (with A. R. Hurd) Org. Lett. 1999, 1, 1311-1314.

[161] Enantioselective Total Syntheses of (+)-Castanospermine, (+)-6-Epicastanospermine, (+)-Australine, and (+)-3-Epiaustraline (with E. A. Martinborough) J. Am. Chem. Soc. 1999, 121, 3046-3056.

[159] The Tandem Cycloaddition Chemistry of Nitroalkenes: Probing the Remarkable Stereochemical Influence of the Lewis Acid (with M. Seierstad) J. Org. Chem. 1999, 64, 1610-1619.

[158] The Tandem Cycloaddition Chemistry of Nitroalkenes: Preparative and Theoretical Studies on the Stereochemical Course of [3 + 2] Cycloaddition of Cyclic Nitronates (with M. J. Seierstad and B. Herbert) J. Org. Chem. 1999, 64, 884-901.

[153] Tandem Inter [4+2]/Intra [3+2] Cycloadditions of Nitroalkenes. Asymmetric Synthesis of Highly Functionalized Aminocyclopentanes Using the Bridged Mode beta-Tether Process (with J. A. Dixon) J. Org. Chem. 1998, 63, 6178-6195.

[152] Tandem Inter [4+2]/Intra [3+2] Cycloadditions of Nitroalkenes. The Bridged Mode b -Tether (with J. A. Dixon) J. Org. Chem. 1998, 63, 6167-6177.

[150] The Synthesis of (1R,2R,3R,7R,7aR) – Hexahydro-3-(hydroxymethyl) – 1H-pyrrolizine-1,2,7-triol, “7-Epiaustraline” (with B. Herbert) J. Am. Chem. Soc . 1998 , 120, 7357-7358.

[148] Tandem Inter [4+2]/Intra [3+2] Cycloadditions with Nitroethylene (with A. R. Hurd) J. Org. Chem. 1998, 63, 3045-3050.

[144] Tandem Inter [4+2]/Intra [3+2] Cycloadditions. 17. The Spiro Mode. Efficient and Highly Selective Synthesis of Azapropellanes (with D. S. Middleton) J. Org. Chem. 1998, 63, 1604-1618.

[140] Tandem Inter [4+2]/Intra [3+2] Cycloadditions of Nitroalkenes. A Versatile Asymmetric Synthesis of Highly Functionalized Aminocyclopentanes. (with J. A. Dixon) J. Org. Chem. 1997, 62, 7086-7087.

[137] Tandem Inter [4+2]/Intra [3+2] Cycloadditions of Nitroalkenes. 15. The Bridged Mode alpha-Tether (with V. Guagnano, J. A. Dixon and A. Stolle) J. Org. Chem. 1997, 62, 4610-4628.

[134] Asymmetric Construction of a Quaternary Carbon Center by Tandem [4+2]/[3+2] Cycloadditions of Nitroalkenes. The Total Synthesis of (–)-Mesembrine (with L. R. Marcin) J. Org. Chem. 1997, 62, 1675-1686.

[133] Tandem [4+2]/[3+2] Cycloadditions of Nitroalkenes. 13. The Synthesis of (-)-Detoxinine (with A. R. Hurd and H. J. Sacha) J. Org. Chem. 1997, 62,1668-1674.

[130] Tandem [4+2]/[3+2] Cycloadditions of Nitroalkenes. 12. Synthesis of (–)-Platynecine (with D. L. Parker and J. A Dixon) J. Org. Chem. 1997, 62, 435-436.

[129] Tandem Inter [4+2]/Intra [3+2] Cycloadditions. 11. The Synthesis of (+)-Crotanecine (with A. Thorarensen) J. Am. Chem. Soc. 1997, 119, 125-137.

[126] rel-(1R. 6S, 7S, 8R, 9S) – 9-Methyl- 8 -phenyl- 6 -[1(1S,2R) – (2-phenylcyclohexyl)oxy] – 4-aza-3,5-dioxatricyclo[5.2.1.0 4,9]decane (with K. A. Swiss and J. A. Dixon) Acta Cryst C. 1996, C52, 2561-2563.

[125] 2aS, 3S, 6S, 7S, 7bR)- 7 -[(Dimethylphenyl) – silyl]- 2 -oxo-6-[(1R,2S)- 2 -phenylcyclo-hexyloxy] – 2a,3,6,7,7a,7b – hexahydro-2H-1.4.5 – trioxa-4a – azaxyxlopenta[cd]indene- 3 -carboxylic Acid 1-Methyethyl Ester (with A. Thorarensen and K. A. Swiss) Acta Cryst C. 1996, C52, 2558-2561.

[123] Tandem [4+2]/[3+2] Cycloadditions of Nitroalkenes. 10. trans-2-(1-Methyl-1-Phenylethyl)-cyclohexanol as a New Auxiliary (with A. Thorarensen) J. Org. Chem. 1996, 61, 6727-6729.

[122] Tandem [4+2]/[3+2] Cycloadditions of Nitroalkenes. 9. The Synthesis of (–)-Rosmarinecine (with A. Thorarensen and D. S. Middleton) J. Am. Chem. Soc. 1996, 118, 8266-8277.

[121] Tandem Inter [4+2]/Intra [3+2] Cycloadditions. 8. Unactivated Dipolarophiles (with C. B. W. Senanayake) Tetrahedron 1996, 52, 11579-11600.

[117] Tandem [4+2]/[3+2] Cycloadditions of Nitroalkenes (with A. Thorarensen) Chem. Rev. 1996, 96, 137-165.

[111] A General Strategy for the Synthesis of Cis-Substituted Pyrrolizidine Bases. The Synthesis of (–)-Rosmarinecine (with A. Thorarensen and D. S. Middleton) J. Org. Chem. 1995, 60, 3574-3575.

[110] Asymmetric Nitroalkene [4+2] Cycloadditions: Enantioselective Synthesis of 3-Substituted and 3,4-Disubstituted Pyrrolidines (with L. R. Marcin) J. Org. Chem. 1995, 60, 3221-3235.

[109] Nitroalkene Inter [4+2]/Intra [3+2] Tandem Cycloadditions. 7. Application of (R)-(–)-2,2-Diphenylcyclopentanol as the Chiral Auxiliary (with M. E. Schnute, L. R. Marcin, and A. Thorarensen) J. Org. Chem. 1995, 60, 3205-3220.

[103] Tandem Inter [4+2]/Intra [3+2] Cycloadditions. 6. The Bridged Mode (with A. Stolle, and J. A. Dixon and V. Guagnano) J. Am. Chem. Soc. 1995, 117, 2100-2101.

[100] The Tandem Cycloaddition Chemistry of Nitroalkenes (with M. E. Schnute, A. Thorarensen, D. S. Middleton, and A. Stolle) Pure Appl. Chem. 1994, 66, 2041-2044.

[99] The Tandem Cycloaddition Chemistry of Nitroalkenes. A Novel Synthesis of (–)-Hastanecine (with A. Thorarensen) J. Org. Chem. 1994, 59, 5672-5680.

[94] Nitroalkene [4+2] Cycloadditions with 2-Acyloxyvinyl Ethers. Stereoselective Synthesis of 3-Hydroxy-4-Substituted Pyrrolidines (with M. E. Schnute) J. Org. Chem. 1994, 59, 4576-4595. 

[86] Nitroalkene [4+2] Cycloaddition as a General and Stereoselective Route to 3,3- and 3,4-Disubstituted Pyrrolidines (with L. R. Marcin) J. Org. Chem. 1993, 58 , 3857-3868.

[85] A General Method for the Preparation of 2,2-Disubstituted 1-Nitroalkenes (with L. R. Marcin) J. Org. Chem. 1993, 58 , 3850-3856.

[81] Tandem Inter [4+2]/Intra [3+2] Cycloadditions. 5. Origin of the Lewis Acid Dependent Reversal of Stereoselectivity (with M. E. Schnute and C. B. W. Senanayake) J. Org. Chem. 1993, 58, 1859-1874.

[80] Tandem Inter [4+2]/Intra [3+2] Cycloadditions. 4. Cycloadditions with E- and Z-1-Propenyl Ethers (with C. B. W. Senanayake) J. Org. Chem. 1993, 58, 1853-1858.

[76] The Tandem Cycloaddition Chemistry of Nitroalkenes (with M. E. Schnute, C. B. W. Senanayake, Y.-C. Moon and D. S. Middleton) Proceedings of the 5th International Kyoto Conference on New Aspects of Organic Chemistry; Z.-I. Yoshida and Y. Ohshiro, Eds.; Kodansha Press, 1992, pp. 215-239.

[73] Inter- and Intramolecular [4+2]-Cycloadditions of Nitroalkenes with Olefins. 2-Nitrostyrenes (with B. S. Kesler and Y.-C. Moon) J. Org. Chem. 1992, 57, 4912-4924.

[65] Tandem Inter [4+2]/Intra [3+2] Cycloadditions. 3. The Stereochemical Influence of the Lewis Acid (with M. E. Schnute) J. Org. Chem. 1991, 56, 6738-6739.

[51] Intramolecular [4+2]-Cycloaddition of Nitroalkenes with Olefins. 2 (with Y.-C. Moon, C. J. Cramer, M. S. Dappen and C. B. W. Senanayake) Tetrahedron 1990, 46, 7373-7392.

[50] Tandem [4+2]/[3+2]-Cycloadditions. 2. Asymmetric Induction with a Chiral Vinyl Ether (with C. B. W. Senanayake and G.-D. Ho) Tetrahedron 1990, 46, 4857-4876.

[45] Tandem [4+2]/[3+2] Cycloadditions: Facile and Stereoselective Construction of Polycyclic Frameworks (with Y.-C. Moon and C. B. W. Senanayake) J. Am. Chem. Soc. 1990, 112, 311-316.

[24] Intramolecular [4+2]-Cycloadditions of Vinylnitrosonium Cations with Olefins (with C. J. Cramer and M. S. Dappen) J. Org. Chem. 1987, 52, 877-887.

[20] The Stereostructures of [1,1′-Bicyclohexyl]-2,2′-diones: A Reassignment (with C. J. Cramer and J. A. Sternberg) Tetrahedron Lett. 1986, 27, 3693-3696.

[18] Intramolecular [4+2] Cycloadditions of Nitroalkenes with Olefins (with M. S. Dappen and C. J. Cramer) J. Am. Chem. Soc. 1986, 108, 1306-1307.

[15] Intramolecular [4+2] Cycloadditions of Nitrosoalkenes with Olefins (with M. S. Dappen and J. A. Sternberg) J. Org. Chem. 1984, 49, 4741-4743.

[12] alpha -Chloro Ketoximes as Precursors of Nitrosoalkenes: Preparation, Stereochemistry, and Conformation (with M. S. Dappen) J. Org. Chem. 1984, 49, 798-806.