Linear polystyrene anchored l-proline, new recyclable organocatalysts for the aldol reaction in the presence of water

Liu, Yuxia; Sun, Yanan; Tan, Haohan; Liu, Wei; Tao, Jing‐Chao

doi:10.1016/j.tetasy.2007.10.032

Cited by 62 publications

(23 citation statements)

References 57 publications

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“…When the same reaction conditions were applied to the reaction of acetone or 2-butanone with aromatic aldehydes, lower yields and diastereoselectivies were achieved, albeit the enantioselectivities levels were maintained. The polymeric resins could be reused up to five times, a slightly decrease on the reactivity being observed [65,66]. In all the above described systems, the catalytic moiety was anchored to a commercially available or a conveniently functionalized synthetic polymer.…”

Section: Aqueous Aldol Reactions With Supported Organocatalystsmentioning

confidence: 99%

Pursuing Chemical Efficiency by Using Supported Organocatalysts for Asymmetric Reactions under Aqueous Conditions

Guillena

Alonso²,

Baeza³

et al. 2015

COCAT

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Over the past decade, a great effort has been made by the chemical community to improve the efficiency and greenness of reactions. Merging the use of supported and recyclable organocatalysts and aqueous conditions to pursue this goal in the asymmetric synthesis of interesting enantioselective molecules lead to outstanding results in some cases. Progresses in this area also offer the possibility of having even more sustainable processes by implementing these reactions in the large scale production of chiral molecules using automated flow chemistry.

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Section: Aqueous Aldol Reactions With Supported Organocatalystsmentioning

confidence: 99%

Pursuing Chemical Efficiency by Using Supported Organocatalysts for Asymmetric Reactions under Aqueous Conditions

Guillena

Alonso²,

Baeza³

et al. 2015

COCAT

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show abstract

“…85,86 The catalysts 48-50 all afforded products in moderate yield (ca. 60-70%) with excellent ee values in the 90-98% range and served as recoverable catalysts for asymmetric aldol reactions.…”

Section: Ncps-bound Organocatalystsmentioning

confidence: 99%

Using Soluble Polymer Supports To Facilitate Homogeneous Catalysis

2009

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“…[2g,4d,5] The polymer supports with designed compositions, topologies, and functionalities can offer prolines and their derivatives (or other organocatalysts) specific catalytic microenvironments, comparable to those found in natural enzymes. [2g,4d] Polymeric scaffolds, including linear homopolymers [6,7] , linear random [8] or block copolymers, [9] dendrimers, [10] and styrenic [11,12] or acrylic resins, [13] have been developed. [5] Numerous investigations have been reported in the preparation of polymer-supported L-prolines and their derivatives.…”

Section: Introductionmentioning

confidence: 99%

Hyperbranched polyethylene-supported l-proline: a highly selective and recyclable organocatalyst for asymmetric aldol reactions

Wang

Liu

Wang

et al. 2015

Catal. Sci. Technol.

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A novel hyperbranched polyethylene (HBPE)-supported L-proline has been developed via a bottom-up copolymerization strategy. The copolymerization of ethylene and protected proline acrylate comonomer with cationic Pd-diimine catalysts was conducted, followed by de-protection of the proline groups. Well-defined HBPE copolymers having molecular weights (MWs) of 10.3-50.3 kDa and 3.2-15.6 L-proline molecules per HBPE polymer chain were synthesized. The effects of the L-proline amount and HBPE MW on the catalyst performance were studied. The HBPE catalysts were efficient in asymmetric Aldol reactions of p-nitrobenzaldehyde (p-NBA) or benzaldehyde derivatives with cyclohexanone. High p-NBA conversions of up to 98% and excellent product selectivities with anti/syn = 98/2 and ee>99% were achieved. Moreover, the HBPE catalysts could be easily reclaimed by adding water into the product. The reclaimed catalysts could be reused for multiple times with only a slight decline in reactivity and selectivity.

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Linear polystyrene anchored l-proline, new recyclable organocatalysts for the aldol reaction in the presence of water

Cited by 62 publications

References 57 publications

Pursuing Chemical Efficiency by Using Supported Organocatalysts for Asymmetric Reactions under Aqueous Conditions

Pursuing Chemical Efficiency by Using Supported Organocatalysts for Asymmetric Reactions under Aqueous Conditions

Using Soluble Polymer Supports To Facilitate Homogeneous Catalysis

Hyperbranched polyethylene-supported l-proline: a highly selective and recyclable organocatalyst for asymmetric aldol reactions

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