Synthesis 2016; 48(16): 2627-2636
DOI: 10.1055/s-0035-1561421
special topic
© Georg Thieme Verlag Stuttgart · New York

Catalytic Enantioselective Alkynylation of Tetrahydroisoquinoline-Based N-Acyl Hemiaminals

Shutao Sun
a   School of Pharmaceutical Sciences, Shandong University, Jinan 250012, P. R. of China
,
Lei Liu*
a   School of Pharmaceutical Sciences, Shandong University, Jinan 250012, P. R. of China
b   Key Lab for Colloid and Interface Chemistry of Education Ministry, School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, P. R. of China   eMail: leiliu@sdu.edu.cn
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Publikationsverlauf

Received: 15. Januar 2016

Accepted after revision: 23. Februar 2016

Publikationsdatum:
07. April 2016 (online)


Abstract

A highly enantioselective catalytic alkynylation of tetrahydroisoquinoline-based N-acyl hemiaminals has been developed. The method is simple and exhibits a broad scope with respect to both heterocycles and terminal alkynes, thus allowing for facile construction of a variety of enantiopure α-substituted tetrahydroisoquinolines.

Supporting Information

 
  • References

    • 1a Shamma M, Moniot JL. The Isoquinoline Alkaloids, Chemistry and Pharmacology . Academic Press; New York: 1972
    • 1b Herbert RB In The Chemistry and Biology of Isoquinoline Alkaloids . Philipson JD, Roberts MF, Zenk MH. Springer Verlag; Berlin: 1985: 213
  • 2 Taylor AM, Schreiber SL. Org. Lett. 2006; 8: 143
    • 3a Black DA, Beveridge RE, Arndtsen BA. J. Org. Chem. 2008; 73: 1906
    • 3b Sun Z, Yu S, Ding Z, Ma D. J. Am. Chem. Soc. 2007; 129: 9300
    • 4a Li Z, Li C.-J. Org. Lett. 2004; 6: 4997
    • 4b Li Z, MacLeod PD, Li C.-J. Tetrahedron: Asymmetry 2006; 17: 590
  • 5 Hashimoto T, Omote M, Maruoka K. Angew. Chem. Int. Ed. 2011; 50: 8952
  • 6 Lin W, Cao T, Fan W, Han Y, Kuang J, Luo H, Miao B, Tang X, Yu Q, Yuan W, Zhang J, Zhu C, Ma S. Angew. Chem. Int. Ed. 2014; 53: 277
  • 7 Sun S, Li C, Floreancig PE, Lou H, Liu L. Org. Lett. 2015; 17: 1684
    • 8a Sasamoto N, Dubs C, Hamashima Y, Sodeoka M. J. Am. Chem. Soc. 2006; 128: 14010
    • 8b Christian D, Yoshitaka H, Naoki S, Seidel TM, Suzuki S, Hashizume D, Sodeoka M. J. Org. Chem. 2008; 73: 5859
    • 8c Guo C, Song J, Luo S.-W, Gong L.-Z. Angew. Chem. Int. Ed. 2010; 49: 5558
    • 8d Zhang G, Zhang Y, Wang R. Angew. Chem. Int. Ed. 2011; 50: 10429
    • 8e Zhang J, Tiwari B, Xing C, Chen X, Chi YR. Angew. Chem. Int. Ed. 2012; 51: 3649
    • 8f Zhang G, Ma Y, Wang S, Zhang Y, Wang R. J. Am. Chem. Soc. 2012; 134: 12334
    • 8g Zhang G, Ma Y, Wang S, Kong W, Wang R. Chem. Sci. 2013; 4: 2645
    • 8h Neel AJ, Hehn JP, Tripet PF, Toste FD. J. Am. Chem. Soc. 2013; 135: 14044
    • 8i Bergonzini G, Schindler CS, Wallentin C.-J, Jacobsen EN, Stephenson CR. J. Chem. Sci. 2014; 5: 112
    • 8j Wei X.-H, Wang G.-W, Yang S.-D. Chem. Commun. 2015; 51: 832
    • 8k Mengozzi L, Gualandi A, Cozzi PG. Chem. Sci. 2014; 5: 3915
    • 8l Chau ST, Lutz JP, Wu K, Doyle AG. Angew. Chem. Int. Ed. 2013; 52: 9153
    • 8m Gualandi A, Mengozzi L, Manoni E, Cozzi PG. Catal. Lett. 2015; 145: 398
    • 8n Nakamura M, Hirai A, Nakamura E. J. Am. Chem. Soc. 1996; 118: 8489
    • 8o Taylor MS, Tokunaga N, Jacobsen EN. Angew. Chem. Int. Ed. 2005; 44: 6700
    • 9a Murahashi S.-I, Naota T, Yonemura K. J. Am. Chem. Soc. 1988; 110: 8256
    • 9b Shi S.-L, Wei X.-F, Shimizu Y, Kanai M. J. Am. Chem. Soc. 2012; 134: 17019
    • 9c Sueda T, Kajishima D, Goto S. J. Org. Chem. 2003; 68: 3307
    • 9d Kashdan DS, Schwartz JA, Rapoport H. J. Org. Chem. 1982; 47: 2638
    • 9e Schweitzer-Chaput B, Klussmann M. Eur. J. Org. Chem. 2013; 666
    • 10a Meng Z, Sun S, Yuan H, Lou H, Liu L. Angew. Chem. Int. Ed. 2004; 53: 543
    • 10b Liu X, Meng Z, Lou H, Liu L. Angew. Chem. Int. Ed. 2015; 54: 6012
    • 10c Liu X, Sun S, Meng Z, Lou H, Liu L. Org. Lett. 2015; 17: 2396
    • 10d Sun S, Mao Y, Lou H, Liu L. Chem. Commun. 2015; 51: 10691
  • 11 Maity P, Srinivas HD, Watson MP. J. Am. Chem. Soc. 2011; 133: 17142
    • 12a Taylor SJ, Taylor AM, Schreiber SL. Angew. Chem. Int. Ed. 2004; 43: 1681
    • 12b Burke MD, Schreiber SL. Angew. Chem. Int. Ed. 2004; 43: 46