A General Approach to Aza‐Heterocycles by Means of Domino Sequences Driven by Hydroformylation

Airiau, Etienne; Spangenberg, Thomas; Girard, Nicolas; Schoenfelder, Angèle; Salvadori, Jessica; Taddei, Maurizio; Mann, André

doi:10.1002/chem.200801795

Cited by 49 publications

(26 citation statements)

References 39 publications

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“…The chemoselective HF of 86 in CH 2 Cl 2 and TFA at 55 C for 12 h affords an intermediate enamide which directly undergoes an Aza-Sakurai Hosomi's reaction with the formation of 87 in good yield and stereoselectivity. Working in the same reaction conditions, just changing the acid (BF 3 OEt 2 ) and the solvent (THF) used, a further HF of 87 occurs, 88 being isolated as the only reaction product (Scheme 16) [39]. With the developed protocols, two cycles and nine new bonds are formed in the same chemical operation.…”

Section: Cyclohydrocarbonylation (Chc)mentioning

confidence: 97%

“…Mann and Taddei widely explored CHC for stereoselective synthesis of heterocyclic compounds in cascade with other transformations such as: CHC/aza-Sakurai Hosomi, CHC/aza-Sakurai Hosomi/HF, and CHC/Pictect-Spengler [39]. Proper design of the starting materials, obtained by decoration of 3-butenoic acid with different chiral auxiliaries, enables a certain control on the new stereogenic centres generated during the reaction cascade.…”

Section: Cyclohydrocarbonylation (Chc)mentioning

confidence: 98%

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Domino Reactions Triggered by Hydroformylation

Petricci

Cini

2013

Topics in Current Chemistry

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Section: Cyclohydrocarbonylation (Chc)mentioning

confidence: 97%

Section: Cyclohydrocarbonylation (Chc)mentioning

confidence: 98%

Domino Reactions Triggered by Hydroformylation

Petricci

Cini

2013

Topics in Current Chemistry

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“…Гідроформілювання вторинних амідів 51 у при-сутності родійвмісної каталітичної системи при-водить до альдегіду 52, який за рахунок внутріш-ньомолекулярної конденсації перетворюється на N-ацилімінієвий інтермедіат А, нуклеофільна ата-ка гідроксильної групи в якому сприяє формуван-ню оксазолопіперидону 53 [29] (схема 20).…”

Section: схемаunclassified

Heterocyclization of amides of alkenylcarboxylic acids

Tsyzoryk¹,

Васькевич²,

Вовк³

2015

J. org. pharm. chem.

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(Ховейда, Граббса, Нолана), реакції мета-тезису, а також радикальних процесів у регіо-та стереоселективних циклізаціях амідів у м'яких умовах. Розглянуті синтетичні варіанти носять загальний характер і дозволяють поряд із процесами циклізації здійснювати спрямовану функціоналізацію O-, N-, S-вмісних малих та середніх гетероциклічних систем. HETEROCYCLIZATION OF AMIDES OF ALKENYLCARBOXYLIC ACIDS N.M.Tsyzoryk, A.I.Vaskevich, M.V.Vovk Key words: amides of alkenylcarboxylic acids; electrophilic intramolecular cyclization; lactones; lactams The latest published data on heterocyclization of amides of alkenylcarboxylic acids have been systematized. It has been proven that the electrophilic intramolecular cyclization reaction of functionally substituted olefins opened in the 70s of the last century is a convenient way of constructing different oxygen-, nitrogen-and sulfurcontaining heterocyclic compounds. It has been noted that anilides of unsaturated carboxylic acids as bifunctional nucleophilic systems containing alkenyl and aminocarbonyl functions are useful models to study the electrophilic cyclization reaction, which leads to formation of O-and N-containing heterocycles (lactones and lactams). The last of them belong to the important types of compounds used as key blocks in the synthesis of biologically active alkaloids and their analogues, pharmaceutical and agrochemical products. The effective approaches to the synthesis of new types of functionalized lactones and lactams have been developed; amides of 3-butenoic, 4-pentenoic and 5-hexenoic acids are often used as substrates for their design. Along with classical methods of synthesis of lactones and lactams the literary sources relating to the use of original catalytic electrophilic systems (Nolan, Grubbs, Hoveyda), the metathesis reaction and radical processes in regio-and stereoselective cyclization of amides under mild conditions have been analyzed and summarized in the article. The synthetic versions considered are general in nature and allow to perform the targeted functionalization of O-, N-, S-containing heterocyclic small and medium-sized systems along with the cyclization processes. ГЕТЕРОЦИКЛИЗАЦИИ АМИДОВ АЛКЕНИЛКАРБОНОВЫХ КИСЛОТ

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“…The reaction of diphenylprolinol (34) with butanal (2) gave the corresponding aminonitriles (i.e., 45a-b) in quantitative yield, and in all other cases, variable amounts of aldehyde cyanohydrins and starting materials could be detected in the crude reaction mixtures, and the products had to be purified by flash chromatography, thus lowering the yields.…”

Section: Secondary Chiral Aminesmentioning

confidence: 99%

“…Reaction intermediates and models for the asymmetric induction. [24] To obtain some evidence about the intermediates involved in our catalyst-free one-pot reaction in water, NMR analysis was performed with benzaldehyde (1), butanal (2), l-prolinol (33), and l-diphenylprolinol (34). [22] Computational studies on the effect of the structure of the amine on the formation of iminium intermediates with aldehydes in water showed that aminol and iminum species were intermediates with high barriers, especially for secondary cyclic amines such as proline methyl ester and pyrrolidine.…”

Section: Secondary Chiral Aminesmentioning

confidence: 99%

Asymmetric Strecker Reaction with Chiral Amines: a Catalyst‐Free Protocol Using Acetone Cyanohydrin in Water

et al. 2013

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The synthesis of a series of new chiral α‐aminonitriles was achieved in a diastereoselective Strecker reaction in a one‐pot procedure with aldehydes, enantiopure amines, and acetone cyanohydrin in water. Primary and secondary amines derived from L‐α‐amino acids were used as sources of chirality. The reactions proceeded efficiently without any catalyst at room temperature. The diastereoselectivity of the process, and the configurational stability of new chiral α‐aminonitriles were investigated. The identification of labile intermediates by NMR analysis, and a proposed mechanism and a model for the asymmetric induction are reported. The chemical transformation of proline‐derived chiral α‐amino‐nitriles into chiral amino‐diacids, aminols, and amides is reported.

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A General Approach to Aza‐Heterocycles by Means of Domino Sequences Driven by Hydroformylation

Cited by 49 publications

References 39 publications

Domino Reactions Triggered by Hydroformylation

Domino Reactions Triggered by Hydroformylation

Heterocyclization of amides of alkenylcarboxylic acids

Asymmetric Strecker Reaction with Chiral Amines: a Catalyst‐Free Protocol Using Acetone Cyanohydrin in Water

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