Synthesis 2016; 48(04): 512-519
DOI: 10.1055/s-0035-1561276
feature
© Georg Thieme Verlag Stuttgart · New York

Gold(I)-Catalyzed Stereospecific [4+3]-Cycloaddition Reaction of 1-(Alk-1-ynyl)cyclopropyl Ketones with Nitrones: A Modular Entry to Enantioenriched 5,7-Fused Bicyclic Furo[3,4-d][1,2]oxazepines

Yanqing Zhang
a  Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, 3663 N. Zhongshan Road, Shanghai, 200062, P. R. of China   eMail: yjxiao@chem.ecnu.edu.cn
b  Patent Examination Cooperation Jiangsu Center of the Patent Office, Sipo, 88N. Guangqi Road, Suzhou, Jiangsu 215163, P. R. of China
,
Yuanjing Xiao*
a  Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, 3663 N. Zhongshan Road, Shanghai, 200062, P. R. of China   eMail: yjxiao@chem.ecnu.edu.cn
,
Junliang Zhang*
a  Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, 3663 N. Zhongshan Road, Shanghai, 200062, P. R. of China   eMail: yjxiao@chem.ecnu.edu.cn
c  State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, CAS. 345 Lingling Road, Shanghai, 200032, P. R. of China   eMail: jlzhang@chem.ecnu.edu.cn
› Institutsangaben
Weitere Informationen

Publikationsverlauf

Received: 12. Oktober 2015

Accepted after revision: 06. November 2015

Publikationsdatum:
11. Januar 2016 (online)


Abstract

In our previous study, a gold(I)-catalyzed stereoselective formal [4+3]-cycloaddition reaction of 1-(alk-1-ynyl)cyclopropyl ketones with nitrones was found to afford 5,7-fused bicyclic furo[3,4-d][1,2]oxazepines in good to excellent yields with high diastereoselectivity catalyzed by (triphenylphosphine)gold(I) triflate. In order to gain insight into the mechanism of this [4+3] cycloaddition process, an enantioselective version used a MeO-DTBM-BIPHEP derived gold(I) complex as the catalyst, which resulted in the kinetic resolution of the 1-(alk-1-ynyl)cyclopropyl ketones, affording the recovered ketones in high yield with excellent enantioselectivity. An interesting chirality transfer was observed in the gold(I)-catalyzed [4+3] cycloaddition of optically active 1-(alk-1-ynyl)cyclopropyl ketones with nitrones, indicating the reaction undergoes a stereospecific SN2-type ring-opening of the cyclopropane.

Supporting Information

 
  • References

  • 1 Lu B.-L, Dai L, Shi M. Chem. Soc. Rev. 2012; 41: 3318
  • 2 Zhang J, Schmalz H.-G. Angew. Chem. Int. Ed. 2006; 45: 6704
    • 3a Zhang G, Huang X, Li G, Zhang L. J. Am. Chem. Soc. 2008; 130: 1814
    • 3b Li G, Huang X, Zhang L. J. Am. Chem. Soc. 2008; 130: 6944
  • 4 Zhang Y, Chen Z, Xiao Y, Zhang J. Chem. Eur. J. 2009; 15: 5208
  • 5 Liu F, Yu Y, Zhang J. Angew. Chem. Int. Ed. 2009; 48: 5505
    • 6a Gao H, Zhang J. Adv. Synth. Catal. 2009; 351: 85
    • 6b Xiao Y, Zhang J. Chem. Commun. 2009; 3594
    • 6c Liu L, Zhang J. Angew. Chem. Int. Ed. 2009; 48: 6093
    • 6d Zhou G, Zhang J. Chem. Commun. 2010; 46: 6593
    • 6e Chen Z, Tian Z, Zhang J.-M, Zhang J. Chem. Eur. J. 2012; 18: 8591
    • 6f Zeng Q, Zhang L, Yang J, Xu B, Xiao Y, Zhang J. Chem. Commun. 2014; 50: 4203
    • 7a Zhang Y, Liu F, Zhang J. Chem. Eur. J. 2010; 16: 6146
    • 7b Bai Y, Fang J, Ren J, Wang Z. Chem. Eur. J. 2009; 15: 8975
  • 8 Part of this work has been published in a preliminary communication, see: Zhang Y, Zhang J. Chem. Commun. 2012; 48: 4710

    • For Lewis acid catalyzed (dynamic) kinetic resolutions of cyclopropane diesters, see:
    • 9a Sibi MP, Ma Z, Jasperse CP. J. Am. Chem. Soc. 2005; 127: 5764
    • 9b Kang Y.-B, Sun X.-L, Tang Y. Angew. Chem. Int. Ed. 2007; 46: 3918
    • 9c Parsonsand AT, Johnson JS. J. Am. Chem. Soc. 2009; 131: 3122
    • 9d Parsons AT, Smith AG, Neel AJ, Johnson JS. J. Am. Chem. Soc. 2010; 132: 9688
    • 9e Campbell MJ, Johnson JS, Parsons AT, Pohlhaus PD, Sanders SD. J. Org. Chem. 2010; 75: 6317 . Note, however, that these reported catalytic systems are not applied to the present 1-(alk-1-ynyl)cyclopropyl ketones
    • 10a Johansson MJ, Gorin DJ, Staben ST, Toste FD. J. Am. Chem. Soc. 2005; 127: 18002
    • 10b Watson ID. G, Ritter S, Toste FD. J. Am. Chem. Soc. 2009; 131: 2056
    • 10c Cao Z.-Y, Wang X, Tan C, Zhao X.-L, Zhou J, Ding K. J. Am. Chem. Soc. 2013; 135: 8197
    • 10d Briones JF, Davies HM. L. J. Am. Chem. Soc. 2012; 134: 11916

      For selected reviews on gold-catalyzed reactions published since 2011, see:
    • 11a Bandini M. Chem. Soc. Rev. 2011; 40: 1358
    • 11b Krause N, Winter C. Chem. Rev. 2011; 111: 1994
    • 11c Haro TD, Nevado C. Synthesis 2011; 2530
    • 11d Wegner HA, Auias M. Angew. Chem. Int. Ed. 2011; 50: 8236
    • 11e Boorman TC, Larrosa I. Chem. Soc. Rev. 2011; 40: 1910
    • 11f Rudolph M, Hashmi AS. K. Chem. Commun. 2011; 47: 6536
    • 11g Gaillard S, Cazin CS. J, Nolan SP. Acc. Chem. Res. 2012; 45: 778
    • 11h Rudolph M, Hashmi AS. K. Chem. Soc. Rev. 2012; 41: 2448
    • 11i Zhang D, Zhang Z, Shi M. Chem. Commun. 2012; 48: 10271
    • 11j Haibach MC, Seidel D. Angew. Chem. Int. Ed. 2014; 53: 5010
    • 11k Zhang L. Acc. Chem. Res. 2014; 47: 877
    • 11l Xie J, Pan C, Abdukade A, Zhu CJ. Chem. Soc. Rev. 2014; 43: 5245
    • 11m Obradors C, Echavarren AM. Chem. Commun. 2014; 50: 16
    • 11n Hashmi AS. K. Acc. Chem. Res. 2014; 47: 864
    • 11o Obradors C, Echavarren AM. Acc. Chem. Res. 2014; 47: 902
    • 11p Zhang D, Tang X, Shi M. Acc. Chem. Res. 2014; 47: 913
    • 11q Fürstner A. Acc. Chem. Res. 2014; 47: 925
    • 11r Alcaide B, Almendros P. Acc. Chem. Res. 2014; 47: 939
    • 11s Fensterbank L, Malacria M. Acc. Chem. Res. 2014; 47: 953
    • 11t Yeom H.-S, Shin S. Acc. Chem. Res. 2014; 47: 966
    • 11u Qian D, Zhang J. Chem. Rec. 2014; 14: 280
    • 11v Jia M, Bandini M. ACS Catal. 2015; 5: 1638
    • 11w Qian D, Zhang J. Chem. Soc. Rev. 2015; 44: 677
    • 11x Ranieri B, Escofet I, Echavarren AM. Org. Biomol. Chem. 2015; 13: 7130
    • 11y Dorel R, Echavarren AM. Chem. Rev. 2015; 115: 9028

      For recent general reviews on non-enzymatic kinetic resolution, see:
    • 12a Pellissier H. Adv. Synth. Catal. 2011; 353: 1613
    • 12b Vedejs E, Jure M. Angew. Chem. Int. Ed. 2005; 44: 3974

      For selected reviews on enantioselective gold(I) catalysis, see:
    • 13a Widenhoefer RA. Chem. Eur. J. 2008; 14: 5382
    • 13b Bongers N, Krause N. Angew. Chem. Int. Ed. 2008; 47: 2178
    • 13c Senguptaand S, Shi X. ChemCatChem 2010; 2: 609
    • 13d Pradal A, Toullec PY, Michelet V. Synthesis 2011; 1501
    • 13e Cera G, Bandini M. Isr. J. Chem. 2013; 53: 848
    • 13f Wang Y, Lackner AD, Toster FD. Acc. Chem. Res. 2014; 47: 889
    • 13g Abadie M.-A, Medina L, Agbossou-Niedercorn F, Michon C. Chim. Oggi 2014; 32: 19
    • 13h Nájera C, Sansano JM. J. Organomet. Chem. 2014; 771: 78

    • For very recent examples, see:
    • 13i Du Y, Hu Y, Zhu Y, Tu X, Han Z, Gong L.-Z. J. Org. Chem. 2015; 80: 4754
    • 13j Oka J, Okamoto R, Noguchi K, Tanaka K. Org. Lett. 2015; 17: 676
    • 13k Jia M, Monari M, Yang Q, Bandini M. Chem. Commun. 2015; 51: 2320
    • 13l Ji K, Zheng Z, Wang Z, Zhang L. Angew. Chem. Int. Ed 2015; 54: 1245
    • 14a Liu F, Qian D, Li L, Zhao X, Zhang J. Angew. Chem. Int. Ed 2010; 49: 6669
    • 14b Zhou G, Liu F, Zhang J. Chem. Eur. J. 2011; 17: 3101
    • 14c Zhang Z, Chen P, Li W, Niu Y, Zhao X, Zhang J. Angew. Chem. Int. Ed 2014; 53: 4350
    • 14d Qian D, Hu H, Liu F, Tang B, Ye W, Wang Y, Zhang J. Angew. Chem. Int. Ed 2014; 53: 13751
    • 14e Liu F, Wang Y, Ye W, Zhang J. Org. Chem. Front. 2015; 2: 221
    • 14f Wang YD, Zhang P, Liu Y, Xia F, Zhang J. Chem. Sci. 2015; 6: 5564
  • 15 CCDC 837843 contains the supplementary crystallographic data for (1R,4R)-3ib. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.
    • 16a Labsch S, Ye S, Adler A, Neudörfl J.-M, Schmalz H.-G. Tetrahedron: Asymmetry 2010; 21: 1745

    • For DFT studies on the mechanism and regioselectivity of the gold(I)-catalyzed reactions of 1-(alk-1-ynyl)cyclopropyl ketones with nucleophiles (ref. 2), see:
    • 16b Fang R, Su C.-Y, Zhao C, Phillips DL. Organometallics 2009; 28: 741
    • 16c Zhang J, Shen W, Li L, Li M. Organometallics 2009; 28: 3129
  • 17 Dondoni A, Franco S, Junquera F, Merchan F, Merino P, Tejero T. Synth. Commun. 1994; 24: 2537