Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2010(20): 3474-3480
DOI: 10.1055/s-0030-1258204
DOI: 10.1055/s-0030-1258204
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkSynthesis of Tetrahydroisoquinolines via Cascade Reductive Amination of Isochromenylium Tetrafluoroborate with Primary Amines
Further Information
Received
28 May 2010
Publication Date:
13 August 2010 (online)
Publication History
Publication Date:
13 August 2010 (online)

Abstract
Reactions of isochromenylium tetrafluoroborates with various primary amines have been investigated under reductive amination conditions. The established cascade methodology provides a convenient one-step synthesis of various tetrahydroisoquinoline derivatives under mild conditions.
Key words
isochromenylium - reductive amination - tetrahydroisoquinoline - heterocycle - cascade reaction
- Supporting Information for this article is available online:
- Supporting Information
- 1a
Tovar JD.Swager TM. J. Org. Chem. 1999, 64: 6499MissingFormLabel - 1b
Shen HC. Tetrahedron 2008, 64: 7847MissingFormLabel - 1c
Kim N.Kim Y.Park W.Sung D.Gupta AK.Oh CH. Org. Lett. 2005, 7: 5289MissingFormLabel - 2a
Singh V.Krishna UM.Vikrant V.Trivedi GK. Tetrahedron 2008, 64: 3405MissingFormLabel - 2b
Li GT.Huang XG.Zhang LM. Angew. Chem. Int. Ed. 2008, 47: 346MissingFormLabel - 3
Patil NT.Yamamoto Y. Chem. Rev. 2008, 108: 3395 - 4
Arcadi A. Chem. Rev. 2008, 108: 3266 - 5
Li ZG.Brouwer C.He C. Chem. Rev. 2008, 108: 3239 - 6a
Jin TN.Yamamoto Y. Org. Lett. 2007, 9: 5259MissingFormLabel - 6b
Pale P.Chuche J. Eur. J. Org. Chem. 2000, 1019MissingFormLabel - 7a
Qian W.-J.Wei W.-G.Zhang Y.-X.Yao Z.-J. J. Am. Chem. Soc. 2007, 129: 6400MissingFormLabel - 7b
Hiroya K.Itoh S.Sakamoto T. J. Org. Chem. 2004, 69: 1126MissingFormLabel - 7c
Asao N.Nogami T.Takahashi K.Yamamoto Y. J. Am. Chem. Soc. 2002, 124: 764MissingFormLabel - 8a
Zhu JL.Grigoriadis NP.Lee JP.Porco JA.
J. Am. Chem. Soc. 2005, 127: 9342MissingFormLabel - 8b
Bruneau C.Dixneuf PH. Acc. Chem. Res. 1999, 32: 311MissingFormLabel - 9a
Dyker G.Hildebrandt D. J. Org. Chem. 2005, 70: 6093MissingFormLabel - 9b
Hildebrandt D.Hüggenberg W.Kanthak M.Dyker G. Chem. Commun. 2006, 2260MissingFormLabel - 10a
Hildebrandt D.Dyker G. J. Org. Chem. 2006, 71: 6728MissingFormLabel - 10b
Kusama H.Ishida K.Funami H.Iwasawa N. Angew. Chem. Int. Ed. 2008, 47: 4903MissingFormLabel - 11
Hu Z.-L.Qian W.-J.Wang S.Wang S.-Z.Yao Z.-J. Org. Lett. 2009, 11: 4676 - 12
Hu Z.-L.Qian W.-J.Wang S.Wang S.-Z.Yao Z.-J.
J. Org. Chem. 2009, 74: 8787 - 13
Hu Z.-L.Qian W.-J.Yao Z.-J. Sci. China Chem. 2010, 53: 869 - 14
Wei W.-G.Yao Z.-J. J. Org. Chem. 2005, 70: 4585 - 15
Prauda I.Tóth-Lauritz M.Reiter J. J. Heterocycl. Chem. 2004, 41: 915 - Recent reviews on natural alkaloids containing the tetrahydroisoquinoline core, such as renieramycin G, jorumycin, saframycins, ecteinascidin 743 (ET 743) etc., see:
- 16a
Scott JD.Williams RM. Chem. Rev. 2002, 102: 1669MissingFormLabel - 16b
Siengalewicz P.Rinner U.Mulzer J. Chem. Soc. Rev. 2008, 37: 2676MissingFormLabel - 18
Hwang S.Lee Y.Shin S.Lee PH. Tetrahedron Lett. 2009, 50: 2305
References
Two diastereomeric isomers were observed in ¹³C NMR spectrum of 4c (all carbon peaks are reported in the experimental section), but they were homogeneous in the ¹H NMR spectrum.