Asymmetric Iodolactamization Induced by Chiral Oxazolidine Auxiliary

Shen, Mei‐Hua; Li, Chaozhong

doi:10.1021/jo0488006

Cited by 53 publications

(15 citation statements)

References 24 publications

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“…Автори [49] вперше розробили метод асиме-тричної індукованої γ-йодолактамізації. З цією Регіоселективна йодоциклізація ненасичених амідів 90 проходить у присутності LiAl(O-Bu-t) 4 і приводить до йодометилпіролідинону 91 [50] (схема 36).…”

Section: циклізації амідів 4-пентенових кислотunclassified

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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Section: циклізації амідів 4-пентенових кислотunclassified

Heterocyclization of amides of alkenylcarboxylic acids

Tsyzoryk¹,

Васькевич²,

Вовк³

2015

J. org. pharm. chem.

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“…The use of chiral auxiliaries for asymmetric introduction of halogen atoms onto olefins has only been explored in a limited fashion, using Oppolzers sultam, [9] oxazolidines [10] and oxazolidinones, [11] for example. Diastereomeric ratios are typically poor (< 4:1); however, the products should be readily separable and should provide a way to generate halogenated building blocks in enantiomerically pure form, after auxiliary removal.…”

Section: Diastereoselective Halogenation Of Olefinsmentioning

confidence: 99%

Current Methods for Asymmetric Halogenation of Olefins

Castellanos

Fletcher

2011

Chemistry A European J

271

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“…[1] Enantioenriched 1,3-oxazolidines are also commonly utilized as chiral auxiliaries in pharmaceutical synthesis as well as ligands in transition metal catalysis. [2] Consequently, stereospecific and stereoconvergent synthetic methods toward optically active 1,3-oxazolidines have been extensively explored over the last decades. [3] However, the synthesis of chiral oxazolidine derivatives fused with nitrogen heterocycles has not been studied.…”

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Asymmetric Synthesis of N‐Fused 1,3‐Oxazolidines via Pd‐Catalyzed Decarboxylative (3+2) Cycloaddition

et al. 2020

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Efficient synthesis of optically active Nfused 1,3-oxazolidines containing quaternary and tertiary stereocenters was achieved via Pd-catalyzed asymmetric (3 + 2) cycloadditions of sulfamatederived cyclic imines and vinylethylene carbonates. Using a chiral phosphoramidite ligand, the cycloadditions proceeded effectively providing sulfamidate-fused 1,3-oxazolidines in high yields (up to 96%) with stereoselectivities (up to 25:1 dr; > 99% ee). Additionally, the scale-up reaction and further transformations of the product were also achieved demonstrating the synthetic utility toward the construction of useful heterocycles such as chiral oxazoline bearing a quaternary stereocenter.Scheme 2. Gram-scale synthesis of sulfamidate-fused 1,3-oxazolidine 3 a and its further applications.

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Asymmetric Iodolactamization Induced by Chiral Oxazolidine Auxiliary

Cited by 53 publications

References 24 publications

Heterocyclization of amides of alkenylcarboxylic acids

Heterocyclization of amides of alkenylcarboxylic acids

Current Methods for Asymmetric Halogenation of Olefins

Asymmetric Synthesis of N‐Fused 1,3‐Oxazolidines via Pd‐Catalyzed Decarboxylative (3+2) Cycloaddition

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