A convergent synthesis of enantiopure bicyclic scaffolds through multicomponent Ugi reaction

Banfi, Luca; Basso, Andrea; Guanti, Giuseppe; Merlo, Silvia; Repetto, Claudio; Riva, Renata

doi:10.1016/j.tet.2007.10.058

Cited by 53 publications

(35 citation statements)

References 59 publications

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“…The synthesis of lactams, namely hexahydropyrrolodiazepinediones, by this approach is displayed in Scheme 25. 55 In this case the carboxylic component is a protected b-alanine, either unsubstituted (104) or a-substituted with a protected amino group (105). After Ugi condensations, which proceed in good yields and ca.…”

Section: Scheme 24mentioning

confidence: 99%

“…A simple, high-yielding, three-step protocol, involving amide → imide conversion, deprotection of the additional protected amine and cyclization, afforded the hexahydropyrrolodiazepinediones 109a,b. 55 Although the diversity point derived from the isocyanide is lost in this sequence, the hydroxymethyl appendage remains free for further manipulations (including oxidation at the carboxy level). From a stereochemical point of view, this approach is in part complementary to the one outlined in Scheme 25.…”

Section: One Additional Functionmentioning

confidence: 99%

See 1 more Smart Citation

Coupling Isocyanide-Based Multicomponent Reactions with Aliphatic or Acyl Nucleophilic Substitution Processes

Banfi¹,

Riva²,

Basso³

2009

Synlett

Self Cite

112

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This account summarizes the results of studies carried out by the authors during the last 10 years aimed at expanding the utility of the venerable Passerini and Ugi reactions. Particular emphasis is given to efforts that focus on coupling these processes with post-condensation, intramolecular, aliphatic nucleophilic substitution and acyl nucleophilic substitution reactions. The methodologies developed in these investigations serve as the basis for short sequences for the preparation of a diverse number of interesting drug-like structures.

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Section: Scheme 24mentioning

confidence: 99%

Section: One Additional Functionmentioning

confidence: 99%

Coupling Isocyanide-Based Multicomponent Reactions with Aliphatic or Acyl Nucleophilic Substitution Processes

Banfi¹,

Riva²,

Basso³

2009

Synlett

Self Cite

112

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“…Examples of 1,3-induction on chiral imines with the stereocentre β to the carbon [14,16], or α to the nitrogen, of the C=N moiety [13,15,17] are rarer. More often, when the stereocentre is not in α, poor diastereoselectivity is observed [18–19]. This fact limits the diversity of heterocycles that can be accessed stereoselectively from the three-component Ugi–Joullié reaction of cyclic imines.…”

Section: Introductionmentioning

confidence: 99%

Long-range diastereoselectivity in Ugi reactions of 2-substituted dihydrobenzoxazepines

Banfi¹,

Basso²,

Cerulli³

et al. 2011

Beilstein J. Org. Chem.

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SummaryThe Ugi reaction of 2-substituted dihydrobenzoxazepines was found to proceed with unexpectedly good diastereoselectivitiy (diastereoisomeric ratios up to 9:1), despite the large distance between the pre-existing stereogenic centre and the newly generated one. This result represents the first good 1,4 asymmetric induction in an Ugi reaction as well as the first example of diastereoselective Ugi reaction of seven membered cyclic imines. It allows the diversity-oriented synthesis of various tetrahydro[f][1,4]benzoxazepines.

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“…153 On the other hand, the corresponding enantiomerically pure N-acyl-2,5-disubstituted pyrrolidines were produced in moderate to high yields (47-85%). These products were employed as key intermediates in the synthesis of two series of enantiopure bicyclic derivatives, namely hexahydro pyrrolo-oxazocinediones and -diazepinediones.…”

Section: Multicomponent Reactions Based On the Ugi Reactionmentioning

confidence: 99%

Asymmetric Domino Reactions Based on the Use of Chiral Substrates

2013

Asymmetric Domino Reactions

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This chapter updates the recent developments in asymmetric one-, two-, and multicomponent domino reactions which involve chiral substrates. It is divided into two sections, dealing successively with one- and two-component domino reactions, and with multicomponent domino reactions. The first section is subdivided into eight sections, describing domino reactions with an anionic primary step, domino reactions based on cationic sequences, domino reactions initiated by a pericyclic primary step, domino reactions based on carbene sequences, palladium-catalysed domino reactions, ruthenium-catalysed domino reactions, gold-catalysed domino reactions, and finally miscellaneous domino reactions. The second section of the chapter is subdivided into 10 sections, dealing with multicomponent reactions initiated by the Michael addition, multicomponent reactions based on the Hantzsch reaction, multicomponent reactions based on the Ugi reaction, multicomponent reactions based on the Strecker reaction, multicomponent reactions based on the Mannich reaction, multicomponent reactions initiated by an allylation reaction, multicomponent reactions based on the Passerini reaction, multicomponent reactions based on the Biginelli reaction, multicomponent reactions based on the Petasis reaction, and finally miscellaneous multicomponent reactions. The power and utility of these reactions are well illustrated by their application in the synthesis of a wide range of structurally diverse and complex chiral molecules.

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A convergent synthesis of enantiopure bicyclic scaffolds through multicomponent Ugi reaction

Cited by 53 publications

References 59 publications

Coupling Isocyanide-Based Multicomponent Reactions with Aliphatic or Acyl Nucleophilic Substitution Processes

Coupling Isocyanide-Based Multicomponent Reactions with Aliphatic or Acyl Nucleophilic Substitution Processes

Long-range diastereoselectivity in Ugi reactions of 2-substituted dihydrobenzoxazepines

Asymmetric Domino Reactions Based on the Use of Chiral Substrates

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