Synthesis 2016; 48(16): 2619-2626
DOI: 10.1055/s-0035-1561958
special topic
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Synthesis of Dipropionate Derivatives through Catalytic Hydrogenation of Enantioenriched E-Ketene Heterodimers

Shi Chen
a  Department of Chemistry, Oakland University, 2200 N. Squirrel Road, Rochester, MI 48309-4477, USA   Email: kerrigan@oakland.edu
,
Mukulesh Mondal
a  Department of Chemistry, Oakland University, 2200 N. Squirrel Road, Rochester, MI 48309-4477, USA   Email: kerrigan@oakland.edu
,
Ahmad A. Ibrahim
a  Department of Chemistry, Oakland University, 2200 N. Squirrel Road, Rochester, MI 48309-4477, USA   Email: kerrigan@oakland.edu
,
Kraig A. Wheeler
b  Department of Chemistry, Eastern Illinois University, 600 Lincoln Avenue, Charleston, IL 61920-3099, USA
,
Nessan J. Kerrigan*
a  Department of Chemistry, Oakland University, 2200 N. Squirrel Road, Rochester, MI 48309-4477, USA   Email: kerrigan@oakland.edu
› Author Affiliations
Further Information

Publication History

Received: 11 January 2016

Accepted after revision: 02 March 2016

Publication Date:
12 April 2016 (online)

Abstract

A highly diastereoselective approach to dipropionate derivatives through Pd/C-catalyzed hydrogenation of enantioenriched E-ketene heterodimers is described. Catalytic hydrogenation of the E-isomer of ketene heterodimer β-lactones (12 examples) provides access to syn,anti-β-lactones (dipropionate derivatives) bearing up to three stereogenic centers (dr up to 49:1), and with excellent transfer of chirality (ee up to >99%).

Supporting Information

 
  • References

  • 1 New address: Ahmad A. Ibrahim, Department of Chemistry, Wayne State University, 5101 Cass Ave., Detroit, MI 48202, USA.
    • 2a Yeung KS, Paterson I. Chem. Rev. 2005; 105: 4237
    • 2b Schetter B, Mahrwald R. Angew. Chem. Int. Ed. 2006; 45: 7506
    • 2c Arefolov A, Panek JS. J. Am. Chem. Soc. 2005; 127: 5596
    • 2d Keck GE, Knutson CE, Wiles SA. Org. Lett. 2001; 3: 707
    • 3a ter Horst B, Feringa BL, Minnaard AJ. Chem. Commun. 2010; 46: 2535
    • 3b Hanessian S, Giroux S, Mascitti V. Synthesis 2006; 1057
    • 4a Roush WR. J. Org. Chem. 1991; 56: 4151
    • 4b Masamune S, Choy W, Petersen JS, Sita LR. Angew. Chem., Int. Ed. Engl. 1985; 24: 1
    • 5a Yamamoto Y, Asao N. Chem. Rev. 1993; 93: 2207
    • 5b Denmark SE, Fu J. Chem. Rev. 2003; 103: 2763
    • 5c Roush WR, Palkowitz AD, Ando K. J. Am. Chem. Soc. 1990; 112: 6348
    • 5d Lachance H, Hall DG. Org. React. 2008; 73: 1
    • 6a Evans DA, Dart MJ, Duffy JL, Rieger DL. J. Am. Chem. Soc. 1995; 117: 9073
    • 6b Evans DA, Sheppard GS. J. Org. Chem. 1990; 55: 5192
    • 6c Evans DA, Clark JS, Metternich R, Novack VJ, Sheppard GS. J. Am. Chem. Soc. 1990; 112: 866
  • 7 Paterson I. Pure Appl. Chem. 1992; 64: 1821
  • 8 Chen M, Roush WR. J. Am. Chem. Soc. 2012; 134: 3925
  • 9 Shen X, Wasmuth AS, Zhao J, Zhu C, Nelson SG. J. Am. Chem. Soc. 2006; 128: 7438
    • 10a Calter MA, Liao W, Struss JA. J. Org. Chem. 2001; 66: 7500
    • 10b Calter MA, Song W, Zhou J. J. Org. Chem. 2004; 69: 1270
  • 11 Casas J, Engqvist M, Ibrahem I, Kaynak B, Córdova A. Angew. Chem. Int. Ed. 2005; 44: 1343
  • 12 Albert BJ, Yamamoto H. Angew. Chem. Int. Ed. 2010; 49: 2747
    • 13a Ibrahim AA, Nalla D, Van Raaphorst M, Kerrigan NJ. J. Am. Chem. Soc. 2012; 134: 2942
    • 13b Ibrahim AA, Wei P.-H, Harzmann GD, Kerrigan NJ. J. Org. Chem. 2010; 75: 7901
    • 13c Ibrahim AA, Harzmann GD, Kerrigan NJ. J. Org. Chem. 2009; 74: 1777
    • 13d Marqués-López E, Christmann M. Angew. Chem. Int. Ed. 2012; 51: 8696
    • 13e Chen S, Salo EC, Kerrigan NJ. Asymmetric Organocatalysis 1, Lewis Base and Acid Catalysts . In Science of Synthesis Reference Library . Vol. 1. List B. Thieme; Stuttgart: 2012. Chap. 1.1.10, 455
  • 14 Chen S, Ibrahim AA, Mondal M, Magee AJ, Cruz AJ, Wheeler KA, Kerrigan NJ. Org. Lett. 2015; 17: 3248
  • 15 Purohit VC, Richardson RD, Smith JW, Romo D. J. Org. Chem. 2006; 71: 4549
    • 16a Brown JM. Angew. Chem., Int. Ed. Engl. 1987; 26: 190
    • 16b Cui X, Burgess K. Chem. Rev. 2005; 105: 3272
    • 16c Woodmansee DH, Pfaltz A. Chem. Commun. 2011; 47: 7912
  • 17 Yu J, Spencer JB. Tetrahedron 1998; 54: 15821
  • 18 Hoffman RW. Chem. Rev. 1989; 89: 1841
  • 19 Armarego WL. F, Perrin DD. Purification of Laboratory Chemicals . 4th ed. Butterworth-Heinemann; Oxford: 2002
    • 20a Hodous BL, Fu GC. J. Am. Chem. Soc. 2002; 124: 10006
    • 20b Wiskur SL, Fu GC. J. Am. Chem. Soc. 2005; 127: 6176
    • 20c Allen AD, Baigrie LM, Gong L, Tidwell TT. Can. J. Chem. 1991; 69: 138
    • 20d Wilson JE, Fu GC. Angew. Chem. Int. Ed. 2004; 43: 6358
    • 20e Ruden RA. J. Org. Chem. 1974; 39: 3607
    • 21a Papageorgiou CD, Ley SV, Gaunt MJ. Angew. Chem. Int. Ed. 2003; 42: 828
    • 21b Calter MA. J. Org. Chem. 1996; 61: 8006
  • 22 Crystallographic data (excluding structure factors) for (–)-5a have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 1442759.