Isosteviol‐amino Acid Conjugates as Highly Efficient Organocatalysts for the Asymmetric One‐pot Three‐component Mannich Reactions

An, Ya-Jie; Qin, Q.; Wang, Chuanchuan; Tao, Jing‐Chao

doi:10.1002/cjoc.201180272

Cited by 16 publications

(3 citation statements)

References 18 publications

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“…Isosteviol-amino acid conjugates were synthesized and used as chiral catalysts for the asymmetric three-component Mannich reaction with hydroxy acetone as a donor molecule. Good yields (up to 98%) and excellent stereoselectivities (up to 97:3 dr and 99% ee) were achieved in a short reaction time [ 179 ].…”

Section: Other Miscellaneous Usesmentioning

confidence: 99%

Bioactivity Profile of the Diterpene Isosteviol and its Derivatives

et al. 2019

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Steviosides, rebaudiosides and their analogues constitute a major class of naturally occurring biologically active diterpene compounds. The wide spectrum of pharmacological activity of this group of compounds has developed an interest among medicinal chemists to synthesize, purify, and analyze more selective and potent isosteviol derivatives. It has potential biological applications and improves the field of medicinal chemistry by designing novel drugs with the ability to cope against resistance developing diseases. The outstanding advancement in the design and synthesis of isosteviol and its derivative has proved its effectiveness and importance in the field of medicinal chemical research. The present review is an effort to integrate recently developed novel drugs syntheses from isosteviol and potentially active pharmacological importance of the isosteviol derivatives covering the recent advances.

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Section: Other Miscellaneous Usesmentioning

confidence: 99%

Bioactivity Profile of the Diterpene Isosteviol and its Derivatives

et al. 2019

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“…Nevertheless, the skeleton structures to construct thiourea catalysts are very limited, and there is still great demand for novel bifunctional thiourea catalysts for this purpose. Recently, we found that, similar to the cinchona alkaloids, the incorporation of a chiral diterpene moiety (isosteviol) into the thiourea catalysts led to impressive results in asymmetric reactions . Inspired by the excellent chiral structural skeleton of isosteviol, we designed and synthesized a new class of primary amine‐thiourea bifunctional catalysts 3a and 3b .…”

Section: Introductionmentioning

confidence: 99%

“…Recently, we found that, similar to the cinchona alkaloids, the incorporation of a chiral diterpene moiety (isosteviol) into the thiourea catalysts led to impressive results in asymmetric reactions. [31][32][33][34][35][36][37] Inspired by the excellent chiral structural skeleton of isosteviol, we designed and synthesized a new class of primary amine-thiourea bifunctional catalysts 3a and 3b. With these novel catalysts in hand, the effects of the thiourea catalysts were investigated.…”

Section: Introductionmentioning

confidence: 99%

Highly EnantioselectiveMichael Addition Promoted by a New Diterpene‐Derived Bifunctional Thiourea Catalyst: A Doubly Stereocontrolled Approach to Chiral Succinimide Derivatives

Song

Zhang

et al. 2014

Chirality

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A doubly stereocontrolled organocatalytic asymmetric Michael addition to the synthesis of substituted succinimides is described. Starting from aldehydes and maleimides, both enantiomers of the succinimides could be obtained in high to excellent yields (up to 98%) and enantioselectivities (up to 99%) when one of the two special chiral diterpene-derived bifunctional thioureas was individually used as a catalyst. Moreover, these catalysts can be efficiently used in large-scale catalytic synthesis with the same level of yield and enantioselectivity.

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