Heterogeneous catalysis of the asymmetric aldol reaction by solid-supported proline-terminated peptides

Andreae, Marc R. M.; Davis, Anthony P.

doi:10.1016/j.tetasy.2005.06.031

Cited by 89 publications

(26 citation statements)

References 56 publications

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“…[72] . 已经有许多将 PEG 作为有机溶剂或均相催化剂用于氧化反应 [73] 、还原反应 [74] 、Heck 反应 [75] 、aldol 反应 [76] 报道了以 PEG-400 为可回收溶剂下的胺类和哌嗪类与缺电子烯烃的 Michael 加成(Eq. 近年来, 3,4-二氢嘧啶类(DHPMs)引起了人们的特殊关注, 因为它是合成许多杂环化合物的重要砌块 [85] , 并且具有药理活性 [ 8 6 ] .…”

Section: 精(邻磺酰苯甲酰亚胺)型功能离子液体[Bmim][sac] (2)unclassified

Research Progress in the Environmentally-Friendly Michael Addition

Hou¹,

Xu²,

Ying³

et al. 2014

Chin. J. Org. Chem.

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Michael addition is one kind of important reaction in the organic field. With the enhancement of environmental awareness and the depth of green chemistry research, environmentally-friendly Michael addition has made many successes. The research progress over the past 5 years in the Michael addition involving ionic liquids, enzyme catalysis, solid phase supported catalysis and polyethylene glycol (PEG) is reviewed. This paper is consisted of six parts, focusing on the efficiency of the reaction system, the probable catalytic mechanism and the recycle of the catalyst. In the first part, a brief introduction is given. Then the Michael addition used the ionic liquid as catalyst or/and solvent is elaborated. In this part, acidic ionic liquid, basic ionic liquids and chiral ionic liquid are described, respectively. As a mild catalyst, enzymes are described in the third part. The solid phase supported catalysis has been used in many reaction without exception to Michael addition. So, in the fourth part, the catalysts of polymer supported, silica-supported and superparamagnetic nano supported are stated. Following, the successful use of polyethylene glycol (PEG) as a green solvent is presented. Finally, the conclusion, the existing problems of these green technologies and the prospect are summarized.

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Section: 精(邻磺酰苯甲酰亚胺)型功能离子液体[Bmim][sac] (2)unclassified

Research Progress in the Environmentally-Friendly Michael Addition

Hou¹,

Xu²,

Ying³

et al. 2014

Chin. J. Org. Chem.

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“…Subsequently, peptide immobilization undoubtedly represents a strategy for the recovery and reuse of these highly valued compounds. The first example dealing with anchored dipeptides and tripeptides was reported in 2005 by Davis [46], who immobilized a series of peptides onto a Novasyn Tentagel resin 38a-j-an amine-terminated PEG polystyrene graft copolymer. These materials were tested in the aldol reaction between acetone and 4-nitrobenzaldehyde (Scheme 3.13).…”

Section: Polymer Supported Proline-peptidesmentioning

confidence: 99%

Asymmetric Synthesis Using Polymer‐Immobilized Proline Derivatives

Gruttadauria

Giacalone

Noto

2011

Polymeric Chiral Catalyst Design and Chiral Polymer Synthesis

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“…Accordingly, there have been some interesting investigations to apply this concept to proline-catalyzed asymmetric aldol reactions. [149][150][151][152] In designing a catalyst of this type, the essential point is how to expose the active site of the proline catalyst on the polymeric supports. For this purpose, commercially available trans-4-hydroxy-L-proline is frequently used, and some typical examples are shown in Chart 3.…”

Section: Polymer-supported Catalysts and Othersmentioning

confidence: 99%

Organocatalytic Asymmetric Synthesis Using Proline and Related Molecules. Part 2.

Kotsuki¹,

Ikishima²,

Okuyama³

2008

HETEROCYCLES

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-Organocatalytic asymmetric synthesis has been extensively studied and several important procedures for preparing optically active organic compounds have been developed. Research in this area has progressed rapidly in the last ten years. This review addresses the most significant advances in asymmetric synthesis using proline and related chiral organocatalysts mainly focusing on aldol reactions from the viewpoint of synthetic interests. This includes (1) proline-catalyzed aldol reactions, (2) proline-related chiral catalysts, and (3) other types of amino acid catalysts.

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Heterogeneous catalysis of the asymmetric aldol reaction by solid-supported proline-terminated peptides

Cited by 89 publications

References 56 publications

Research Progress in the Environmentally-Friendly Michael Addition

Research Progress in the Environmentally-Friendly Michael Addition

Asymmetric Synthesis Using Polymer‐Immobilized Proline Derivatives

Organocatalytic Asymmetric Synthesis Using Proline and Related Molecules. Part 2.

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