One-Pot Organocatalytic Enantioselective Domino Double-Michael Reaction and Pictet-Spengler–Lactamization Reaction. A Facile Entry to the “Inside Yohimbane” System with Five Contiguous Stereogenic Centers

Hong, Bor‐Cherng; Liao, Wei-Kai; Dange, Nitin S.; Liao, Ju‐Hsiou

doi:10.1021/ol3032329

Cited by 52 publications

(17 citation statements)

References 39 publications

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“…Derivatives of dodecahydrobenz[ a ]indolo[3,2‐ h ]quinolizine ( 109 , inside yohimbane), pro‐aza‐yohimbane ( 111 ), and 7‐azaindole‐octahydroisoquinolin‐3‐one ( 112 , inside‐aza‐yohimbane) were synthesized in excellent stereoselectivities by Hong, Chou, and co‐workers via a double Michael reaction catalyzed by chiral secondary amine ( S )‐ 45 and a successive domino Pictet–Spengler/lactam formation reaction mediated by the Brønsted acid TFA. Compounds 109 and 112 both contain five contiguous stereogenic centers.…”

Section: Primary and Secondary Amine Catalystsmentioning

confidence: 99%

Recent Progress in Organocatalytic Asymmetric Domino Transformations

2017

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Sustainability in chemical synthesis is a major aspect of the current synthetic endeavors and, therefore,m imicking the biological process in the laboratory nowadays has the highest priority.T owards achieving this goal, designingorganic reactions in domino mode rathert han the multistep synthetic pathways andu sing organocatalysisi nstead of metal catalysis have received al ot of attention due to the inherenta dvantageso ft hese processes in terms of synthetic efficiencya nd sustainability.A saresult, the field of asymmetric organocatalytic domino reactions has witnessed tremendous progress in recent years.T his review attempts to summarize the latest developments in asymmetric organocatalyzed domino reactions since 2012, with the emphasis on the catalysts andr eactionm odes.D iscussions on the reactionm echanismsa nd the applications of the developed domino reactionm ethodsi nt he synthesis of biologically active molecules and natural products are also includedwhen appropriate.

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Section: Primary and Secondary Amine Catalystsmentioning

confidence: 99%

Recent Progress in Organocatalytic Asymmetric Domino Transformations

2017

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“…The one-pot domino reaction protocol was repeated with various α,β-unsaturated aldehydes (R 2 = Ar, 2-furyl), obtaining high yields and stereoselectivities. The highly enantioselective transformation and the highly functionalized pentacyclic benzoindoloquinoline products render this reaction sequence a potential protocol for future synthetic applications of "inside α-yohimbane" intermediates [173].…”

Section: Michael Addition/pictet-spengler Reaction Sequences: Update mentioning

confidence: 99%

“…The one-pot domino reaction protocol was repeated with various α,βunsaturated aldehydes (R2 = Ar, 2-furyl), obtaining high yields and stereoselectivities. The highly enantioselective transformation and the highly functionalized pentacyclic benzoindoloquinoline products render this reaction sequence a potential protocol for future synthetic applications of "inside α-yohimbane" intermediates [173]. Menéndez and coworkers highlighted cerium (IV) ammonium nitrate (CAN) as an excellent catalyst for the fast synthesis of β-enaminones 168 [175] and performed the one-pot, efficient preparation of 1-alkyl-6-ethoxy-1,4,5,6-tetrahydropyridines 169 from acyclic precursors, i.e., primary amines 166, β-dicarbonyl compounds 167, α,β-unsaturated aldehydes 145, and alcohols (as sketched in Scheme 49).…”

Section: Michael Addition/pictet-spengler Reaction Sequences: Update mentioning

confidence: 99%

The Pictet-Spengler Reaction Updates Its Habits

et al. 2020

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The Pictet-Spengler reaction (P-S) is one of the most direct, efficient, and variable synthetic method for the construction of privileged pharmacophores such as tetrahydro-isoquinolines (THIQs), tetrahydro-β-carbolines (THBCs), and polyheterocyclic frameworks. In the lustro (five-year period) following its centenary birthday, the P-S reaction did not exit the stage but it came up again on limelight with new features. This review focuses on the interesting results achieved in this period (2011–2015), analyzing the versatility of this reaction. Classic P-S was reported in the total synthesis of complex alkaloids, in combination with chiral catalysts as well as for the generation of libraries of compounds in medicinal chemistry. The P-S has been used also in tandem reactions, with the sequences including ring closing metathesis, isomerization, Michael addition, and Gold- or Brønsted acid-catalyzed N-acyliminium cyclization. Moreover, the combination of P-S reaction with Ugi multicomponent reaction has been exploited for the construction of highly complex polycyclic architectures in few steps and high yields. The P-S reaction has also been successfully employed in solid-phase synthesis, affording products with different structures, including peptidomimetics, synthetic heterocycles, and natural compounds. Finally, the enzymatic version of P-S has been reported for biosynthesis, biotransformations, and bioconjugations.

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“…The procedure was further developed as a one-pot method for the preparation of indolo[2,3-a]quinolizidines [49][50][51] with application in the synthesis of natural products. 52…”

Section: Scheme 17mentioning

confidence: 99%