Synthesis 2014; 46(10): 1367-1373
DOI: 10.1055/s-0033-1340901
special topic
© Georg Thieme Verlag Stuttgart · New York

Asymmetric α-Allylation of α-Branched Aldehydes with Allyl Alcohols by Synergistic Catalysis Using an Achiral Palladium Complex and a Chiral Primary Amino Acid

Masanori Yoshida*
a  Division of Chemical Process Engineering, Faculty of Engineering, Hokkaido University, Kita 13-jo Nishi 8, Kita-ku, Sapporo, Hokkaido 060-8628, Japan
b  Molecular Chemistry and Engineering Course, Graduate School of Chemical Sciences and Engineering, Hokkaido University, Kita 13-jo Nishi 8, Kita-ku, Sapporo, Hokkaido 060-8628, Japan   Fax: +81(11)7066557   Email: myoshida@eng.hokudai.ac.jp
,
Erika Masaki
b  Molecular Chemistry and Engineering Course, Graduate School of Chemical Sciences and Engineering, Hokkaido University, Kita 13-jo Nishi 8, Kita-ku, Sapporo, Hokkaido 060-8628, Japan   Fax: +81(11)7066557   Email: myoshida@eng.hokudai.ac.jp
,
Tatsuaki Terumine
b  Molecular Chemistry and Engineering Course, Graduate School of Chemical Sciences and Engineering, Hokkaido University, Kita 13-jo Nishi 8, Kita-ku, Sapporo, Hokkaido 060-8628, Japan   Fax: +81(11)7066557   Email: myoshida@eng.hokudai.ac.jp
,
Shoji Hara
a  Division of Chemical Process Engineering, Faculty of Engineering, Hokkaido University, Kita 13-jo Nishi 8, Kita-ku, Sapporo, Hokkaido 060-8628, Japan
b  Molecular Chemistry and Engineering Course, Graduate School of Chemical Sciences and Engineering, Hokkaido University, Kita 13-jo Nishi 8, Kita-ku, Sapporo, Hokkaido 060-8628, Japan   Fax: +81(11)7066557   Email: myoshida@eng.hokudai.ac.jp
› Author Affiliations
Further Information

Publication History

Received: 26 December 2013

Accepted after revision: 12 February 2014

Publication Date:
17 March 2014 (online)

Abstract

Highly enantioselective direct α-allylation of α-branched aldehydes with simple allyl alcohols was achieved by the combined use of an achiral transition-metal catalysis with a palladium complex and a chiral organocatalysis with a readily obtainable primary α-amino acid. Various α-allylated aldehydes possessing a stereocontrolled quaternary carbon stereogenic center were synthesized in high yields with high enantioselectivity.

Supporting Information

 
  • References

    • 1a Shimizu M. Angew. Chem. Int. Ed. 2011; 50: 5998
    • 1b Denissova I, Barriault L. Tetrahedron 2003; 59: 10105
    • 1c Christoffers J, Mann A. Angew. Chem. Int. Ed. 2001; 40: 4591
    • 1d Corey EJ, Guzman-Perez A. Angew. Chem. Int. Ed. 1998; 37: 388
    • 1e Fuji K. Chem. Rev. 1993; 93: 2037
    • 1f Martin SF. Tetrahedron 1980; 36: 419
  • 2 Quaternary Stereocenters . Christoffers J, Baro A. Wiley-VCH; Weinheim: 2005

    • Selected reviews on organocatalytic asymmetric Michael addition:
    • 3a Berner OM, Tedeschi L, Enders D. Eur. J. Org. Chem. 2002; 1877
    • 3b Tsogoeva SB. Eur. J. Org. Chem. 2007; 1701
    • 3c Almaşi D, Alonso DA, Nájera C. Tetrahedron: Asymmetry 2007; 18: 299
    • 3d Dalpozzo R, Bartoli G, Bencivenni G. Symmetry 2011; 3: 84
    • 4a Yoshida M, Masaki E, Ikehara H, Hara S. Org. Biomol. Chem. 2012; 10: 5289
    • 4b Yoshida M, Kitamikado N, Ikehara H, Hara S. J. Org. Chem. 2011; 76: 2305
    • 4c Yoshida M, Sato A, Hara S. Org. Biomol. Chem. 2010; 8: 3031
    • 4d Sato A, Yoshida M, Hara S. Chem. Commun. 2008; 6242

      Selected reviews on Tsuji–Trost allylation reaction:
    • 6a Trost BM, Crawley ML. Chem. Rev. 2003; 103: 2921
    • 6b Trost BM. Chem. Rev. 1996; 96: 395
    • 6c Hong AY, Stoltz BM. Eur. J. Org. Chem. 2013; 2745 ; and references therein
    • 7a Murahashi S.-I, Makabe Y, Kunita K. J. Org. Chem. 1988; 53: 4489
    • 7b Hayashi T, Kanehira K, Hagihara T, Kumada M. J. Org. Chem. 1988; 53: 113

      Reviews on catalysis by combined use of organocatalysts and transition-metal catalysts:
    • 8a Zhong C, Shi X. Eur. J. Org. Chem. 2010; 2999
    • 8b Shao Z, Zhang H. Chem. Soc. Rev. 2009; 38: 2745
    • 8c Allen AE, MacMillan DW. C. Chem. Sci. 2012; 3: 633
    • 8d Loh CC. J, Enders D. Chem. Eur. J. 2012; 18: 10212
    • 8e Patil NT, Shinde VS, Gajula B. Org. Biomol. Chem. 2012; 10: 211
    • 8f Zhou J. Chem. Asian J. 2010; 5: 422
    • 9a Ibrahem I, Cόrdova A. Angew. Chem. Int. Ed. 2006; 45: 1952
    • 9b Mukherjee S, List B. J. Am. Chem. Soc. 2007; 129: 11336
    • 9c Jiang G, List B. Angew. Chem. Int. Ed. 2011; 50: 9471
    • 9d Krautwald S, Sarlah D, Schafroth MA, Carreira EM. Science (Washington, D.C.) 2013; 340: 1065
    • 9e Yoshida M, Terumine T, Masaki E, Hara S. J. Org. Chem. 2013; 78: 10853

      Enantioselective allylation of enamines:
    • 10a Weix DJ, Hartwig JF. J. Am. Chem. Soc. 2007; 129: 7720
    • 10b Zhao X, Liu D, Xie F, Zhang W. Tetrahedron 2009; 65: 512
    • 10c Chiarucci M, di Lillo M, Romaniello A, Cozzi PG, Cera G, Bandini M. Chem. Sci. 2012; 3: 2859
    • 10d Xu L.-W, Gao G, Gu F.-L, Sheng H, Li L, Lai G.-Q, Jiang J.-X. Adv. Synth. Catal. 2010; 352: 1441
    • 10e Yasuda S, Kumagai N, Shibasaki M. Heterocycles 2012; 86: 745

      O-Silylated l-serines and l-threonines:
    • 11a Teo Y.-C, Lau J.-J, Wu M.-C. Tetrahedron: Asymmetry 2008; 19: 186
    • 11b Teo Y.-C, Chua G.-L. Tetrahedron Lett. 2008; 49: 4235
    • 11c Wu X, Jiang Z, Shen H.-M, Lu Y. Adv. Synth. Catal. 2007; 349: 812
    • 11d Cheng L, Wu X, Lu Y. Org. Biomol. Chem. 2007; 5: 1018
    • 11e Yoshida M, Narita M, Hirama K, Hara S. Tetrahedron Lett. 2009; 50: 7297

      O-Silylated β-homoserine:
    • 12a Yoshida M, Narita M, Hara S. J. Org. Chem. 2011; 76: 8513
    • 12b Yoshida M, Nagasawa Y, Kubara A, Hara S, Yamanaka M. Tetrahedron 2013; 69: 10003
    • 12c Yoshida M, Kubara A, Hara S. Chem. Lett. 2013; 42: 180
  • 13 Hoffmann S, Nicoletti M, List B. J. Am. Chem. Soc. 2006; 128: 13074