RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2016; 48(16): 2627-2636
DOI: 10.1055/s-0035-1561421
DOI: 10.1055/s-0035-1561421
special topic
Catalytic Enantioselective Alkynylation of Tetrahydroisoquinoline-Based N-Acyl Hemiaminals
Weitere Informationen
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.
Key words
asymmetric catalysis - alkynylation - N-acyl hemiaminals - tetrahydroisoquinolines - dihydroisoquinolinesSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1561421.
- 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