2018
DOI: 10.1002/adsc.201701487
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Reactions Involving Tryptamines and δ‐Allenyl Aldehydes: Competition between Pictet‐Spengler Reaction and Cyclization to 1‐Aminotetralins

Abstract: The isolation of 1-aminotetralin was unexpectedly observed in the course of Pictet-Spengler reactions between tryptamines and dallenyl aldehydes. This discovery led to the study of a novel reactivity using aldehydes and secondary amines. DFT calculations show that the cyclization occurs in a stepwise manner that is sufficiently fast to allow high diastereoselectivity. When using allyltryptamines, it is possible to control the reaction, depending on the substituents, in order to have either the 1-aminotetralin … Show more

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Cited by 17 publications
(3 citation statements)
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“…The metal-dependent regioselectivity of the reaction is best explained by the protodemetalation rate, which is faster with silver than with gold. These important findings resonate together with other works from You (see Section ) or Guinchard (see section ) and picture that the historically proposed 1,2-migration (also invoked in Pictet–Spengler reactions , ) may not be the actual mechanism pathway at stake. Instead, C3-ring closing/ring opening/C2-ring closing equilibria should be more often considered.…”
Section: Gold Catalysissupporting
confidence: 84%
“…The metal-dependent regioselectivity of the reaction is best explained by the protodemetalation rate, which is faster with silver than with gold. These important findings resonate together with other works from You (see Section ) or Guinchard (see section ) and picture that the historically proposed 1,2-migration (also invoked in Pictet–Spengler reactions , ) may not be the actual mechanism pathway at stake. Instead, C3-ring closing/ring opening/C2-ring closing equilibria should be more often considered.…”
Section: Gold Catalysissupporting
confidence: 84%
“…[30][31][32][33][34] Moreover, their mechanistic aspect is intriguing and has been a topic of intensive research for quite a long time. [35][36][37][38][39][40][41][42] In general, two reaction paths are proposed (Scheme 1): the initial iminium ion I generated from the condensation between the corresponding tryptamine and aldehyde might…”
Section: Introductionmentioning
confidence: 99%
“…19 Overall, reactions triggered by direct nucleophilicity of C2 of indoles may often be underestimated, as shown by recent studies. 20 In conclusion, we demonstrated that the regioselective dearomative inter-and intramolecular 3-hydroarylation of indoles could be effected without the need of an activating acetyl group and lead efficiently to the 3-aryl indolines and 5-or 6-membered 3,3-spiroindolines. This redox-neutral addition of a nucleophile into the C3-position of N-H or N-alkyl indoles is very rare and is in sharp contrast with the usual C2-addition of a nucleophile to the transient C2-iminium generated by isomerization of the delocalization of the nitrogen lone pair of N-H or N-alkyle indoles.…”
Section: Scheme 3 Mechanistic Insightsmentioning
confidence: 70%