Citation: Xian-Dong Zhai, Zhong-Duo Yang, Zhi Luo, Hong-Tao Xu. Asymmetric catalyzed intramolecular aza-Michael reaction mediated by quinine-derived primary amines[J]. Chinese Chemical Letters, ;2017, 28(8): 1793-1797. doi: 10.1016/j.cclet.2017.04.017 shu

Asymmetric catalyzed intramolecular aza-Michael reaction mediated by quinine-derived primary amines

a.
School of Life Science and Engineering, Lanzhou University of Technology, Lanzhou 730050, China
b.
Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China

Corresponding author: Zhong-Duo Yang, yangzhongduo@126.com
Received Date: 13 January 2017
Revised Date: 7 April 2017
Accepted Date: 17 April 2017
Available Online: 22 August 2017

Figures(1)

An intramolecular organocatalytic enantioselective aza-Michael reaction of carbamates, sulfonamides and acetamides to α, β-unsaturated ketones was developed. This process is promoted by 9-amino-9-deoxy-epi-quinine and diphenyl hydrogen phosphate to afford a straightforward and expeditious synthesis of several synthetically useful five-and six-membered heterocycles with excellent enantioselectivity (92%-97.5% ee) and very good yields (up to 99%).
- Asymmetric catalysis,
- Intramolecular aza-Michael reaction,
- Primary amine,
- Five-and six-membered heterocycles,
- Pyrrolidine and piperidine,
- Enantioselective organocatalytic
1. [1]
  (a) P. I. Dalko, L. Moisan, In the golden age of organocatalysis, Angew. Chem. Int. Ed. 43(2004) 5138-5175;
  (b) A. Berkessel, H. Groger, Asymmetric Organocatalysis, Wiley-VCH, Weinheim, Germany, 2005;
  (c) Lelais, D. W. C. MacMillan, Modern strategies in organic catalysis: the advent and development of iminium activation, Aldri-Chim. Acta 39(2006) 79-87;
  (d) K. N. Houk, Benjamin List, Asymmetric organocatalysis, Acc. Chem. Res. 37(2004) 487-487.
2. [2]
  (a) B. List, R. A. Lerner, C. F. Barbas Ⅲ, Proline-catalyzed direct asymmetric Aldol reactions, J. Am. Chem. Soc. 122(2000) 2395-2396;
  (b) U. Eder, G. Sauer, R. Wiechert, New type of asymmetric cyclization to optically active steroid CD partial structures, Angew. Chem. Int. Ed. Engl. 10(1971) 496-497;
  (c) Z. G. Hajos, D. R. Parrish, Asymmetric synthesis of bicyclic intermediates of natural product chemistry, J. Org. Chem. 39(1974) 1615-1621.
3. [3]
  (a) S. Mukherjee, J. W. Yang, S. Hoffmann, B. List, Asymmetric enamine catalysis, Chem. Rev. 107(2007) 5471-5569;
  (b) A. Erkkilä, I. Majander, P. M. Pihko, Iminium catalysis, Chem. Rev. 107(2007) 5416-5470.
4. [4]
  L.W. Xu, J. Luo, Y.X. Lu. Asymmetric catalysis with chiral primary amine-based organocatalysts[J]. Chem. Commun., 2009:1807-1821.
5. [5]
  (a) L. Jiang, Y. C. Chen, Recent advances in asymmetric catalysis with cinchona alkaloid-based primary amines, Catal. Sci. Technol. 1(2011) 354-365;
  (b) F. Z. Peng, Z. H. Shao, Advances in asymmetric organocatalytic reactions catalyzed by chiral primary amines, J. Mol. Catal. A 285(2008) 1-13;
  (c) C. Liu, Y. X. Lu, Primary amine/(+)-CSA salt-promoted organocatalytic conjugate addition of nitro esters to enones, Org. Lett. 12(2010) 2278-2281;
  (d) L. T. Dong, R. J. Lu, Q. S. Du, et al. , Highly enantioselective conjugate addition of 1-bromonitroalkanes to alpha, beta-unsaturated ketones catalyzed by 9-amino-9-deoxyepiquinine, Tetrahedron 65(2009) 4124-4129;
  (e) J. Zhou, V. Wakchaure, P. Kraft, B. List, Primary-amine-catalyzed enantioselective intramolecular aldolizations, Angew. Chem. Int. Ed. 47(2008) 7656-7658;
  (f) F. Xue, S. L. Zhang, W. H. Duan, W. Wang, A novel bifunctional sulfonamide primary amine-catalyzed enantioselective conjugate addition of ketones to nitroolefins, Adv. Synth. Catal. 350(2008) 2194-2198;
  (g) S. Z. Luo, H. Xu, L. Zhang, J. Y. Li, J. P. Cheng, Highly enantioselective direct syn-and anti-aldol reactions of dihydroxyacetones catalyzed by chiral primary amine catalysts, Org. Lett. 10(2008) 653-656.
6. [6]
  (a) M. P. Lalonde, Y. Chen, E. N. Jacobsen, A chiral primary amine thiourea catalyst for the highly enantioselective direct conjugate addition of a, a-disubstituted aldehydes to nitroalkenes, Angew. Chem. Int. Ed. 45(2006) 6366-6370;
  (b) S. H. McCooey, S. J. Connon, Readily accessible 9-epi-amino cinchona alkaloid derivatives promote efficient, highly enantioselective additions of aldehydes and ketones to nitroolefins, Org. Lett. 9(2007) 599-602.
7. [7]
  (a) G. Bartoli, P. Melchiorre, A novel organocatalytic tool for the iminium activation of α, β-unsaturated ketones, Synlett 13(2008) 1759-1772;
  (b) Y. C. Chen, The development of asymmetric primary amine catalysts based on cinchona alkaloids, Synlett 13(2008) 1919-1930.
8. [8]
  (a) D. O'Hagan, Pyrrole, pyrrolidine, pyridine, piperidine and tropane alkaloids, Nat. Prod. Rep. 17(2000) 435-446;
  (b) S. Laschat, T. Dickner, Stereoselective synthesis of piperidines, Synthesis (2000) 1781-1813.
9. [9]
  (a) E. C. Juaristi, V. A. Soloshonok, Enantioselective Synthesis of β-Amino Acids, 2nd. ed. , Wiley-VCH Ltd. , New York, 2005;
  (b) J. W. Daly, T. F. Spande, H. M. Garraffo, Alkaloids from amphibian skin: a tabulation of over eight-hundred compounds, J. Nat. Prod. 68(2005) 1556-1575;
  (c) M. G. P. Buffat, Synthesis of piperidines, Tetrahedron 60(2004) 1701-1729;
  (d) P. M. Weintraub, J. S. Sabor, J. M. Kane, D. R. Borcherding, Recent advances in the synthesis of piperidones and piperidines, Tetrahedron 59(2003) 2953-2989;
  (e) M. D. Groaning, A. I. Meyers, Chiral non-racemic bicyclic lactams. Auxiliarybased asymmetric reactions, Tetrahedron 56(2000) 9843-9873;
  (f) S. Leclercq, J. C. Braekman, D. Daloze, J. M. Pasteels, The defensive chemistry of ants, Prog. Chem. Org. Nat. Prod. 79(2000) 115-229;
  (g) J. W. Daly, H. M. Garraffo, T. F. Spende, Alkaloids: chemical and biological perspectives, 14th. ed. , Pergamon, New York, 1999;
  (h) C. Escolano, M. Amat, J. Bosch, Chiral oxazolopiperidone lactams: versatile intermediates for the enantioselective synthesis of piperidine-containing natural products, Chem. Eur. J. 12(2006) 8198-8207;
  (i) M. Schneider, Alkaloids: chemical and biological perspectives, 10th. ed. , Pergamon, New York, 1996;
  (j) H. Xu, H. Tang, H. Feng, Y. Li, Design, synthesis and anticancer activity evaluation of novel C14 heterocycle substituted epi-triptolide, Eur. J. Med. Chem. 73(2014) 46-55.
10. [10]
  (a) B. H. Kim, H. B. Lee, J. K. Hwang, Y. G. Kim, Asymmetric induction in the conjugate addition of thioacetic acid to methacrylamides with chiral auxiliaries, Tetrahedron: Asymmetry 16(2005) 1215-1220;
  (b) M. Nyerges, D. Bendell, A. Arany, et al. , Silver acetate catalysed asymmetric 13-dipolar cycloadditions of imines and chiral acrylamides, Synlett (2003) 947-950;
  (c) F. Fache, E. Schultz, M. L. Tomasino, M. Lemaire, Nitrogen-containing ligands for asymmetric homogeneous and heterogeneous catalysis, Chem. Rev. 100(2000) 2159-2232;
  (d) J. A. Sweet, J. M. Cavallari, W. A. Price, J. W. Ziller, D. V. McGrath, Synthesis and characterization of new amine-imine ligands based on trans-25-disubstituted pyrrolidines, Tetrahedron: Asymmetry 8(1997) 207-211;
  (e) J. K. Whitesell, C2 symmetry and asymmetric induction, Chem. Rev. 89(1989) 1581-1590.
11. [11]
  (a) D. Enders, C. Wang, J. X. Liebich, Organocatalytic asymmetric aza-Michael additions, Chem. Eur. J. 15(2009) 11058-11076;
  (b) J. L. Vicario, D. Badia, L. Carrillo, (+)-(S, S)-Pseudoephedrine as a chiral auxiliary in asymmetric Mannich reactions: scope and limitations, Synthesis (2006) 4065-4074;
  (c) J. L. Vicario, L. Carrillo, J. Etxebarria, E. Reyes, N. Ruiz, The asymmetric azaMichael reaction. a review, Org. Prep. Proced. Int. 37(2005) 513-538;
  (d) L. W. Xu, C. G. Xia, A catalytic enantioselective aza-Michael reaction: novel protocols for asymmetric synthesis of b-amino carbonyl compounds, Eur. J. Org. Chem. (2005) 633-639;
  (e) S. Fustero, J. Moscardo, D. Jimenez, et al. , Organocatalytic approach to benzofused nitrogen-containing heterocycles: enantioselective total synthesis of (+)-angustureine, Chem. Eur. J. 14(2008) 9868-9872;
  (f) M. Bandini, A. Eichholzer, M. Tragni, A. Umani-Ronchi, Enantioselective phase-transfer-catalyzed intramolecular aza-Michael reaction: effective route to pyrazino-indole compounds, Angew. Chem. Int. Ed. 47(2008) 3238-3241;
  (g) S. Fustero, D. Jimenez, J. Moscardo, S. Catalan, C. del Pozo, Enantioselective organocatalytic intramolecular aza-Michael reaction: a concise synthesis of (+)-sedamine. , (+)-allosedamine, and (+)-coniine, Org. Lett. 9(2007) 5283-5286;
  (h) K. Takasu, S. Maiti, M. Ihara, Asymmetric intramolecular aza-Michael reaction using environmentally friendly organocatalysis, Heterocycles 59(2003) 51-55;
  (i) J. D. Liu, Y. C. Chen, G. B. Zhang, et al. , Asymmetric organocatalytic intramolecular aza-Michael addition of enone carbamates: catalytic enantioselective access to functionalized 2-substituted piperidines, Adv. Syn. Catal. 353(2011) 2721-2730;
  (j) L. Y. Wu, G. Bencivenni, M. Mancinelli, et al. , Organocascade reactions of enones catalyzed by a chiral primary amine, Angew. Chem. Int. Ed. 48(2009) 7196-7199;
  (k) B. S. Li, E. Zhang, Q. W. Zhang, et al. , One-pot construction of multisubstituted spiro-cycloalkanediones by an organocatalytic asymmetric epoxidation/semipinacol rearrangement, Chem. Asian J. 6(2011) 2269-2272;
  (l) M. W. Paixao, N. Holub, C. Vila, et al. , Trends in organocatalytic conjugate addition to enones: an efficient approach to optically active alkynyl, alkenyl, and ketone products, Angew. Chem. Int. Ed. 48(2009) 7338-7342;
  (m) W. Chen, W. Du, Y. Z. Duan, et al. , Enantioselective 13-dipolarcycloaddition of cyclic enones catalyzed by multifunctional primary amines: beneficial effects of hydrogen bonding, Angew. Chem. Int. Ed. 46(2007) 7667-7670.
12. [12]
  (a) O. Lifchits, C. M. Reisinger, B. List, Catalytic asymmetric epoxidation of a-branched enals, J. Am. Chem. Soc. 132(2010) 10227-10229;
  (b) C. M. Reisinger, X. Wang, B. List, Catalytic asymmetric hydroperoxidation of α, β-unsaturated ketones: an approach to enantiopure peroxyhemiketals, epoxides, and aldols, Angew. Chem. Int. Ed. 47(2008) 8112-8115;
  (c) X. Tian, C. Cassani, Y. Liu, et al. , Diastereodivergent asymmetric sulfaMichael additions of a-branched enones using a single chiral organic catalyst, J. Am. Chem. Soc. 133(2011) 17934-17941;
  (d) S. Fustero, S. Monteagudo, M. Sanchez-Rosello, et al. , N-Sulfinyl amines as a nitrogen source in the asymmetric intramolecular aza-Michael reaction: total synthesis of (-)-pinidinol, Chem. Eur. J. 16(2010) 9835-9845.
13. [13]
  M.M. Heaton. Quantum mechanical studies of the alpha effect[J]. J. Am. Chem. Soc., 1978,100:2004-2008. doi: 10.1021/ja00475a005
14. [14]
  (a) E. C. Carlson, L. K. Rathbone, H. Yang, N. D. Collett, R. G. Carter, Improved protocol for asymmetric, intramolecular heteroatom Michael addition using organocatalysis: enantioselective syntheses of homoproline, pelletierine, and homopipecolic acid, J. Org. Chem. 73(2008) 5155-5158;
  (b) P. Macours, J. C. Braekman, D. Daloze, Concise asymmetric syntheses of (+)-tetraponerine-8 and (-)-tetraponerine-8, (+)-tetraponerine-7 and (-)-tetraponerine-7, and theirethyl homologs. a correctionof the structuresof tetraponerine-3, and tetraponerine-7, Tetrahedron 51(1995) 1415-1428.
15. [15]
  M.S. Majik, S.G. Tilve. Syntheses of (-)-hygrine and (-)-norhygrine via wacker oxidation[J]. Tetrahedron Lett., 2010,51:2900-2902. doi: 10.1016/j.tetlet.2010.03.098
16. [16]
  H. Takahata, M. Kubota, S. Takahashi, T. Momose. A newasymmetric entry to 2-substituted piperidines. A concise synthesis of (+)-coniine, (-)-pelletierine, (+)-delta-coniceine, and (+)-epidihydropinidine[J]. Tetrahedron:Asymmetry, 1996,7:3047-3054. doi: 10.1016/0957-4166(96)00395-3
17. [17]
  (a) S. G. Davies, A. M. Fletcher, P. M. Roberts, A. D. Smith, Asymmetric synthesisof sedum alkaloids via lithium amide conjugate addition, Tetrahedron 65(2009) 10192-10213;
  (b) I. Coldham, D. Leonori, Regioselective and stereoselective copper(I)-promoted allylation and conjugate addition of N-Boc-2-lithiopyrrolidine and N-Boc-2-lithiopiperidine, J. Org. Chem. 75(2010) 4069-4077.
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