Organic Carbonates from Natural Sources

Zhang, Hua; Liu, Hongbing; Yue, Jian‐Min

doi:10.1021/cr300430e

Cited by 151 publications

(98 citation statements)

References 121 publications

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“…Subsequently, various zinc salts were used as the catalyst in combination with NEt3 for this carboxylative cyclization reaction. In the case of the zinc salts with inorganic oxygen acid as the anion, the catalyst systems ZnCO3/NEt3, Zn(NO3)2/NEt3, Zn(OAc)2/NEt3 and Zn(OTf)2/NEt3 had low catalytic activity for the reaction (Table 1, entries [6][7][8][9]. To our delight, the zinc salts with halogen as the anion could catalyze the reaction effectively in the present of NEt3 (Table 1, entries 10-12).…”

Section: Methodsmentioning

confidence: 99%

Zinc(ii)-catalyzed reactions of carbon dioxide and propargylic alcohols to carbonates at room temperature

Zhu

et al. 2016

Green Chem.

136

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Section: Methodsmentioning

confidence: 99%

Zinc(ii)-catalyzed reactions of carbon dioxide and propargylic alcohols to carbonates at room temperature

Zhu

et al. 2016

Green Chem.

136

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“…Interestingly, a recent review from Yue et al 27 has nicely covered the occurrence of many natural COCs of which the larger part involves di-and tri-substituted carbonate patterns, providing further motivation for the development of catalytic procedures for internal epoxide/CO 2 couplings.…”

Section: Conversion Of Internal Epoxides and Oxetanesmentioning

confidence: 99%

Recent Advances in the Catalytic Preparation of Cyclic Organic Carbonates

2015

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ABSTRACT:The catalytic formation of cyclic organic carbonates (COCs) using carbon dioxide (CO 2 ) as a renewable carbon feed stock is a highly vibrant area of research with an increasing amount of researchers focusing on this thematic investigation. These organic carbonates are highly useful building blocks and nontoxic reagents, and are most commonly derived from CO 2 coupling reactions with oxirane and di-alcohol precursors using homogeneous catalysis methodologies. The activation of suitable reaction partners using catalysis as a key technology is a requisite for efficient CO 2 conversion as its high kinetic stability poses a barrier to access functional organic molecules with added value in both academic and industrial laboratories. Though this area of science has been flourishing for at least a decade, in the last 2−3 years significant advancements have been made to address the general reactivity and selectivity issues that are associated with the formation of COCs. Here we present a concise overview of these activities with a primary focus to highlight the most important progress made and the opportunities that catalysis can bring about when the synthesis of these intermediates is optimized to a higher level of sophistication. The attention will be limited to those cases where homogeneous metal-containing systems have been employed as they possess the highest potential for directed organic synthesis using CO 2 as molecular building block. This review discusses examples of exceptional reactivity and selectivity taking into account the challenging nature of the substrates that were involved, and mechanistic understanding guiding the optimization of these protocols is also highlighted.

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“…The carbonate functionality is therefore very rarely found in natural products 8 . Remarkably, several members of the cytochalasin family of fungal natural products contain an in-line carbonate moiety in the macrocycle portion of the molecules (Fig.1 and Supplementary Results, Supplementary Fig.1).…”

mentioning

confidence: 99%

A carbonate-forming Baeyer-Villiger monooxygenase

Dietrich

et al. 2014

Nat Chem Biol

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Despite the remarkable versatility displayed by flavin-dependent monooxygenases (FMOs) in natural product biosynthesis, one notably missing activity is the oxidative generation of carbonate functional groups. We describe a multifunctional Baeyer-Villiger monooxygenase CcsB, which catalyzes the formation of an in-line carbonate in the macrocyclic portion of cytochalasin E. This study expands the repertoire of activities of FMOs and provides a possible synthetic strategy for transformation of ketones into carbonates.

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Organic Carbonates from Natural Sources

Cited by 151 publications

References 121 publications

Zinc(ii)-catalyzed reactions of carbon dioxide and propargylic alcohols to carbonates at room temperature

Zinc(ii)-catalyzed reactions of carbon dioxide and propargylic alcohols to carbonates at room temperature

Recent Advances in the Catalytic Preparation of Cyclic Organic Carbonates

A carbonate-forming Baeyer-Villiger monooxygenase

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