Synthesis of chiral aza-bis(oxazolines) derived from (+)-camphor

González, Jaime; Martı́nez-Otero, Diego; Frontana‐Uribe, Bernardo A.; Cuevas-Yáñez, Erick

doi:10.1016/j.tetasy.2017.03.001

Cited by 2 publications

(2 citation statements)

References 41 publications

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“…Various derivatives with bornane backbone have found applications as efficient organocatalysts in Pdcatalyzed alkylation, [10] asymmetric Michael addition, [11] and asymmetric cyclopropanation. [12] To date, a number of spirocyclic camphor and fenchone derivatives have been described, including hydantoin and oxazoline, [13] quinazolinone, [14] thiadiazolines, [15] and 1,2,4-triazolidin-3-thions [16] (Figure 2). However, their number is small and this topic is not widely studied.…”

Section: Introductionmentioning

confidence: 99%

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Facile Stereoselective Synthesis and Structural Study of Camphor‐ and Fenchone‐Based Spirocyclic 1,3,4‐Oxadiazolines

Kovaleva,

Abdrakhmanova,

Yarovaya

et al. 2023

Eur J Org Chem

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For the first time, an effective method for the synthesis of spirocyclic camphor‐ and fenchone‐based 1,3,4‐oxadiazolines has been developed. The influence of the molecular structure of the terpene substrate on the reaction stereoselectivity was studied. The structural features of the target products were studied using NMR spectroscopy and X‐ray diffraction analysis. The proposed method allows obtaining of spirocyclic products with a wide structural diversity, stereoselectively and in good yields.

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Section: Introductionmentioning

confidence: 99%

“…To date, a number of spirocyclic camphor and fenchone derivatives have been described, including hydantoin and oxazoline, [13] quinazolinone, [14] thiadiazolines, [15] and 1,2,4‐triazolidin‐3‐thions [16] (Figure 2). However, their number is small and this topic is not widely studied.…”

Section: Introductionmentioning

confidence: 99%

Facile Stereoselective Synthesis and Structural Study of Camphor‐ and Fenchone‐Based Spirocyclic 1,3,4‐Oxadiazolines

Kovaleva,

Abdrakhmanova,

Yarovaya

et al. 2023

Eur J Org Chem

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The Bucherer–Bergs Multicomponent Synthesis of Hydantoins—Excellence in Simplicity

et al. 2021

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Hydantoins and their hybrids with other molecules represent a very important group of heterocycles because they exhibit diverse biological and pharmacological activities in medicinal and agrochemical applications. They also serve as key precursors in the chemical or enzymatic synthesis of significant nonnatural α-amino acids and their conjugates with medical potential. This review provides a comprehensive treatment of the synthesis of hydantoins via the Bucherer–Bergs reaction including the Hoyer modification but limited to free carbonyl compounds or carbonyl compounds protected as acetals (ketals) and cyanohydrins used as starting reaction components. In this respect, the Bucherer–Bergs reaction provides an efficient and simple method in the synthesis of important natural products as well as for the preparation of new organic compounds applicable as potential therapeutics. The scope and limitations, as well as a comparison with some other methods for preparing hydantoins, are also discussed.

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Synthesis of chiral aza-bis(oxazolines) derived from (+)-camphor

Cited by 2 publications

References 41 publications

Facile Stereoselective Synthesis and Structural Study of Camphor‐ and Fenchone‐Based Spirocyclic 1,3,4‐Oxadiazolines

Facile Stereoselective Synthesis and Structural Study of Camphor‐ and Fenchone‐Based Spirocyclic 1,3,4‐Oxadiazolines

The Bucherer–Bergs Multicomponent Synthesis of Hydantoins—Excellence in Simplicity

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