Synthesis 2017; 49(14): 3107-3111
DOI: 10.1055/s-0036-1589023
psp
© Georg Thieme Verlag Stuttgart · New York

Synthesis and Resolution of a Chiral Diamine: 2,2′-(Propane-2,2-diyl)dipyrrolidine

Andreas F. Kotthaus
Bergische Universität Wuppertal, Gaußstr. 20, 42119 Wuppertal, Germany   Email: sfkirsch@uni-wuppertal.de
,
Frederic Ballaschk
Bergische Universität Wuppertal, Gaußstr. 20, 42119 Wuppertal, Germany   Email: sfkirsch@uni-wuppertal.de
,
Vjoni Stakaj
Bergische Universität Wuppertal, Gaußstr. 20, 42119 Wuppertal, Germany   Email: sfkirsch@uni-wuppertal.de
,
Fabian Mohr
Bergische Universität Wuppertal, Gaußstr. 20, 42119 Wuppertal, Germany   Email: sfkirsch@uni-wuppertal.de
,
Bergische Universität Wuppertal, Gaußstr. 20, 42119 Wuppertal, Germany   Email: sfkirsch@uni-wuppertal.de
› Author Affiliations
Further Information

Publication History

Received: 24 March 2017

Accepted after revision: 07 April 2017

Publication Date:
18 May 2017 (online)


Abstract

A short and practical synthesis of a new chiral dipyrrolidine is presented. The three-step route includes a hydrogenation and a resolution with mandelic acid, which easily affords large quantities of the title compound.

Supporting Information

 
  • References

  • 1 Lucet D. Le Gall T. Mioskowski C. Angew. Chem. Int. Ed. 1998; 37: 2580
    • 2a Kizirian J.-C. Chem. Rev. 2008; 108: 140
    • 2b Bennani YL. Hanessian S. Chem. Rev. 1997; 97: 3161
    • 3a Surry DS. Buchwald SL. Chem. Sci. 2010; 1: 13
    • 3b Jin J. Li X. Huang Y. Wu F. Wan B. Chem. Eur. J. 2010; 16: 8259
    • 3c Jia X. Lin A. Mao Z. Zhu C. Cheng Y. Molecules 2011; 16: 2971
    • 3d Denmark SE. Fu J. Lawler MJ. J. Org. Chem. 2006; 71: 1523
    • 3e Jiang X. Gandelman M. J. Am. Chem. Soc. 2015; 137: 2542
    • 3f Scarborough CC. McDonald RI. Hartmann C. Sazama GT. Bergant A. Stahl SS. J. Org. Chem. 2009; 74: 2613
    • 3g Breuning M. Hein D. Steiner M. Gessner VH. Strohmann C. Chem. Eur. J. 2009; 15: 12764
    • 3h Li X. Schenkel LB. Kozlowski MC. Org. Lett. 2000; 2: 875
  • 4 Antilla JC. Klapars A. Buchwald SL. J. Am. Chem. Soc. 2002; 124: 11684
    • 5a Cussó O. Garcia-Bosch I. Ribas X. Lloret-Fillol J. Costas M. J. Am. Chem. Soc. 2013; 135: 14871
    • 5b White MC. Chen MS. Science 2007; 318: 783
  • 6 Carbone C. O’Brien P. Hilmersson G. J. Am. Chem. Soc. 2010; 132: 15445
  • 7 Wagner C. Kotthaus AF. Kirsch SF. Chem. Commun. 2017; 53: 4513
  • 8 Journot G. Neier R. Stoeckli-Evans H. Acta Crystallogr., Sect. E 2010; 66: o392
  • 9 Journot G. Neier R. Stoeckli-Evans H. Acta Crystallogr., Sect. C 2012; 68: o119
  • 10 Klapars A. Antilla JC. Huang X. Buchwald SL. J. Am. Chem. Soc. 2001; 123: 7727
  • 11 For the arylation protocol, see: Shi L. Wang M. Fan C.-A. Zhang F.-M. Tu Y.-Q. Org. Lett. 2003; 5: 3515
    • 12a Patora-Komisarska K. Benohoud M. Ishikawa H. Seebach D. Hayashi Y. Helv. Chim. Acta 2011; 94: 719
    • 12b Seebach D. Sun X. Sparr C. Ebert M.-O. Schweizer WB. Beck AK. Helv. Chim. Acta 2012; 95: 1064
  • 13 Liu J. Liu Q. Yi H. Qin C. Bai R. Qi X. Lan Y. Lei A. Angew. Chem. Int. Ed. 2014; 53: 502
    • 14a Petruzziello D. Gualandi A. Grilli S. Cozzi PG. Eur. J. Org. Chem. 2012; 6697
    • 14b Hayashi Y. Gotoh H. Hayashi T. Shoji M. Angew. Chem. Int. Ed. 2005; 44: 4212
    • 14c Betancort JM. Barbas III CF. Org. Lett. 2001; 3: 3737