2006
DOI: 10.1021/ja057444l
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Catalytic Asymmetric Pictet−Spengler Reaction

Abstract: A catalytic asymmetric Pictet-Spengler reaction has been developed, wherein treating substituted tryptamines with an aldehyde in the presence of a catalytic amount of a chiral phosphoric acid provides the corresponding tetrahydro-beta-carboline derivatives in high yields and enantiomeric excesses. The reaction works well with both aliphatic and aromatic aldehydes.

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Cited by 479 publications
(170 citation statements)
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“…Thus, the first step in indole alkaloids synthesis is thermodynamically and kinetically favored under physiological conditions, and catalysis is required essentially to drive the correct stereochemistry in the ring closure step. In contrast, harsher reaction conditions are required in the case of substituted phenylethyl derivatives because of the lower acidity of the benzenoid proton (27). In this case, the positional contribution of ring substituents and their electron donating or withdrawing effects play a key role in determining the reaction rate of the ring closure step.…”
Section: Discussionmentioning
confidence: 99%
See 1 more Smart Citation
“…Thus, the first step in indole alkaloids synthesis is thermodynamically and kinetically favored under physiological conditions, and catalysis is required essentially to drive the correct stereochemistry in the ring closure step. In contrast, harsher reaction conditions are required in the case of substituted phenylethyl derivatives because of the lower acidity of the benzenoid proton (27). In this case, the positional contribution of ring substituents and their electron donating or withdrawing effects play a key role in determining the reaction rate of the ring closure step.…”
Section: Discussionmentioning
confidence: 99%
“…The enantioselective synthesis of plant indole or benzylisoquinoline alkaloids has always been a challenging task for organic chemists and has led, within the past three decades, to the development of innovative processes in asymmetric synthesis (27,28). In general, the cyclization step of the Pictet-Spengler reaction is a typical acid-basecatalyzed mechanism in which an iminium ion (Schiff base) attacks an electron rich aromatic carbon with subsequent release of the aromatic proton.…”
Section: Discussionmentioning
confidence: 99%
“…The Pictet-Spengler reaction also occurs in solution, although without the presence of a chiral catalyst the reaction is not stereoselective. 58,59 Several strategies were undertaken to probe the mechanism of this enzymatic Pictet-Spengler reaction. First, a primary KIE value was measured for both the enzymatic and solution Pictet-Spengler reactions.…”
Section: Discussionmentioning
confidence: 99%
“…7 Asymmetric Pictet-Spengler reactions have attracted much attention, [8][9][10][11][12][13][14][15] because it is an important and useful tool to construct chiral synthons containing tetrahydro-isoquinoline or tetrahydro-β-carboline (THβC) structural moieties. Therefore, the main challenge of this cyclization is stereoselectivity and the ratio of isomers.…”
Section: Introductionmentioning
confidence: 99%