RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000083.xml
PDF herunterladen
Synlett 2012; 23(7): 1031-1034
DOI: 10.1055/s-0031-1290507
DOI: 10.1055/s-0031-1290507
letter
Primary 1,2-Diamine Catalysis (V): Efficient Asymmetric Aldol Reactions of Isatins with Cyclohexanone
Autoren
Weitere Informationen
Publikationsverlauf
Received: 04. Januar 2012
Accepted after revision: 06. Februar 2012
Publikationsdatum:
16. März 2012 (online)
Abstract
1,2-Diaminocyclohexane-hexanedioic acid has been demonstrated to catalyze the asymmetric aldol reactions of cycloketones and various isatin derivatives efficiently in MeOH–H2O. The corresponding products were obtained in good yields (70–90%) with high diastereoselectivity (up to 99:1 anti/syn) and enantioselectivity (up to 99% ee).
-
References and Notes
- 1a Peddibhotla S. Curr. Bioact. Compd. 2009; 5: 20
- 1b Galliford CV, Scheidt KA. Angew. Chem. Int. Ed. 2007; 46: 8748 ; Angew. Chem. 2007, 119, 8902
- 1c Marti C, Carreira EM. Eur. J. Org. Chem. 2003; 2209
- 1d Kamano Y, Zhang H.-P, Ichihara Y, Kizu H, Komiyama K, Pettit GR. Tetrahedron Lett. 1995; 36: 2783
- 1e Zhang H.-P, Kamano Y, Ichihara Y, Kizu H, Komiyama K, Itokawa H, Pettit GR. Tetrahedron 1995; 51: 5523
- 1f Tang Y.-Q, Sattler I, Thiericke R, Grabley S. Eur. J. Org. Chem. 2001; 66: 261
- 1g Hayashi M, Rho M.-C, Enomoto A, Fukami A, Kim Y.-P, Kikuchi Y, Sunazuka T, Hirose T, Komiyama K, Ōmura S. Proc. Natl. Acad. Sci. U.S.A. 2002; 99: 14728
- 1h Kitajima M, Mori I, Arai K, Kogure N, Takayama H. Tetrahedron Lett. 2006; 47: 3199
- 2a Kamenecka TM, Danishefsky SJ. Chem. Eur. J. 2001; 7: 41
- 2b Nicolaou KC, Rao PB, Hao J, Reddy MV, Rassias G, Huang X, Chen DY.-K, Snyder SA. Angew. Chem. Int. Ed. 2003; 42: 1753
- 2c Liao Y.-J, Wu Y.-L, Chuang C.-P. Tetrahedron 2003; 59: 3511
- 2d Barroso S, Blay G, Cardona L, Fernandez I, Garcia B, Pedro JR. J. Org. Chem. 2004; 69: 6821
- 2e Cleghorn LA. T, Cooper IR, Fishwick CW. G, Grigg R, MacLachlan WS, Rasparini M, Sridharan V. J. Organomet. Chem. 2003; 687: 483
- 2f Schwaebisch D, Tchabanenko K, Adlington RM, Cowley AM, Baldwin JE. Chem. Commun. 2004; 22: 2552
- 2g Luo S, Mi X, Xu H, Wang PG, Cheng J.-P. J. Org. Chem. 2004; 69: 8413
- 2h Hamashima Y, Suzuki T, Takano H, Shimura Y, Sodeoka M. J. Am. Chem. Soc. 2005; 127: 10164
- 2i Toullec PY, Jagt RB. C, De Vries JG, Feringa BL, Minnaard AJ. Org. Lett. 2006; 8: 2715
- 2j Ishimaru T, Shibata N, Nagai J, Nakamura S, Toru T, Kanemasa S. J. Am. Chem. Soc. 2006; 128: 16488
- 2k May JP, Patrick BO, Perrin DM. Synlett 2006; 3403
- 2l Yadav JS, Reddy BV. S, Reddy CS, Krishna AD. Tetrahedron Lett. 2007; 48: 2029
- 2m Sano D, Nagata K, Itoh T. Org. Lett. 2008; 10: 1593
- 2n Durbin MJ, Willis MC. Org. Lett. 2008; 10: 1413
- 2o Kumar CN. S. S. P, Devi CL, Rao VJ, Palaniappan S. Synlett 2008; 2023
- 2p Jia Y.-X, Hillgren JM, Watson EL, Marsden SP, Kundig EP. Chem. Commun. 2008; 34: 4040
- 2q Trost BM, O’Boyle BM. Org. Lett. 2008; 10: 1369
- 2r Lai H, Huang Z, Wu Q, Qin Y. J. Org. Chem. 2009; 74: 283
- 2s Jia Y.-X, Kundig EP. Angew. Chem. Int. Ed. 2009; 48: 1636
- 2t Castaldi MP, Troast DM, Porco JA. Org. Lett. 2009; 11: 3362
- 2u Tsuchikama K, Hashimoto Y, Endo K, Shibata T. Adv. Synth. Catal. 2009; 351: 2850
- 2v Beaumont S, Pons V, Retailleau P, Dodd RH, Dauban P. Angew. Chem. Int. Ed. 2010; 49: 1634
- 2w An G, Zhou W, Zhang G, Sun H, Han J, Pan Y. Org. Lett. 2010; 12: 4482
- 2x Urgaonkar S, Cortese JF, Barker RH, Cromwell M, Serrano AE, Wirth DF, Clardy J, Mazitschek R. Org. Lett. 2010; 12: 3998
- 2y Kothandaraman P, Rao W, Foo SJ, Chan PW. H. Angew. Chem. Int. Ed. 2010; 49: 4619
- 2z Zheng K, Yin C, Liu X, Lin L, Feng X. Angew. Chem. Int. Ed. 2011; 50: 2573
- 3a Corrêa RJ, Garden SJ, Angelici G, Tomasini C. Eur. J. Org. Chem. 2008; 736
- 3b Angelici G, Corrêa RJ, Garden SJ, Tomasini C. Tetrahedron Lett. 2009; 50: 814
- 4a Nakamura S, Hara N, Nakashima H, Kubo K, Shibata N, Toru T. Chem. Eur. J. 2008; 14: 8079
- 4b Hara N, Nakamura S, Shibata N, Toru T. Adv. Synth. Catal. 2010; 352: 1621
- 5 Chen JR, Liu XP, Zhu XY, Li L, Qiao YF, Zhang JM, Xiao WJ. Tetrahedron 2007; 63: 10437
- 6 Malkov AV, Kabeshov MA, Bella M, Kysilka O, Malyshev DA, Pluháčková K, Kočovský P. Org. Lett. 2007; 9: 5473
- 7 Guo Q, Bhanushali M, Zhao CG. Angew. Chem. Int. Ed. 2010; 49: 9460
- 8 Ricci A, Bernardi L, Gioia C, Vierucci S, Robitzer M, Quignard F. Chem. Commun. 2010; 46: 6288
- 9a Raj M, Veerasamy N, Singh V. Tetrahedron Lett. 2010; 51: 2157
- 9b Popp FD, Donigan BE. J. Pharm. Sci. 1979; 68: 519
- 9c Pajouhesh H, Parson R, Popp FD. J. Pharm. Sci. 1983; 72: 318
- 9d Joshi KC, Dandia A, Sanan S. J. Fluorine Chem. 1989; 44: 59
- 10 Wang JF, Qi C, Ge ZM, Cheng TM, Li RT. Chem. Commun. 2010; 46: 2124
- 11 Wang JF, Wang X, Ge ZM, Cheng TM, Li RT. Chem. Commun. 2010; 46: 1751
- 12 Liu Y, Wang JF, Sun Q, Li RT. Tetrahedron Lett. 2011; 52: 3584
- 13 Typical Procedure To the mixed solvent (2 mL, MeOH–H2O = 1:1) was added the corresponding isatin (0.2 mmol), cyclohexanone (0.6 mmol), and catalyst 13 (0.04 mmol) with equal amount of hexanedioic acid (0.04 mmol). The mixture was stirred at r.t. for 14 h, then quenched with additional H2O. The organic matter was extracted with EtOAc, dried over Na2SO4, and the filtrate was concentrated to get the crude product, which was further purified by a silica gel chromatography. 3-Hydroxy-3-(2-oxocyclohexyl)indolin-2-one (16a) Yield 90%; mp 159 °C; anti/syn = 20:1; 99% ee. 1H NMR (400 MHz, DMSO-d 6): δ = 10.16 (s, 1 H), 7.13–7.21 (m, 2 H), 6.75–6.87 (m, 2 H), 5.77 (s, 1 H), 3.07 (dd, J = 12.0, 4.0 Hz, 1 H), 2.53–2.58 (m, 1 H), 2.36–2.53 (m, 1 H), 2.27–2.34 (m, 1 H), 1.58–2.08 (m, 5 H), 1.43–1.50 (m, 1 H). 13C NMR (100 MHz, DMSO-d 6): δ = 209.8, 179.4, 144.1, 131.5, 129.3, 125.5, 121.5, 110.1, 74.6, 58.1, 42.1, 27.4, 27.3, 25.1. HRMS: m/z calcd for C14H16NO3 [M + H+]: 246.11247; found: 246.11184. The enantiomeric ratio was determined by chiral HPLC with AD-H column (hexane–2-PrOH = 80:20, 1 mL/min)