The application of a structurally simple, recyclable, and large-scale l-prolinamide catalyst for asymmetric aldol reactions

A crude extract from earthworms was used as an environmentally friendly and easily accessible biocatalyst for asymmetric direct aldol reactions. The β-hydroxy carbonyl compounds could be prepared in yields of up to 94%, with ee values of up to 98% and dr of up to >99:1. A wide range of substrates could participate in the reaction. This earthworm catalyst was also efficient in the large-scale reaction, providing product in excellent yield and good selectivity. The protocol as an example gives inspiration for the development of sustainable catalysts from nature, which also provides a potential possibility for application of earthworm catalyst in industrial production.

Download Full-text

Efficient synthesis of zirconium poly(styrene-phenylvinylphosphonate)phosphate-supported proline as a recyclable catalyst for direct asymmetric aldol reactions in water

RSC Advances ◽

10.1039/c4ra11208c ◽

2015 ◽

Vol 5 (5) ◽

pp. 3168-3176 ◽

Cited By ~ 6

Author(s):

Chuanlong Wu ◽

Xiaoqin Long ◽

Xiangkai Fu ◽

Guangwei Wang ◽

Zakaria. A. Mirza

Keyword(s):

Large Scale ◽

Recyclable Catalyst ◽

Aldol Reactions ◽

Efficient Synthesis ◽

Asymmetric Aldol

A completely non-chromatographic and highly large-scale adaptable synthesis of zirconium poly(styrene-phenylvinylphosphonate)phosphate-supported l-proline (ZrPS-PVPA-Pr) has been developed in only three steps overall.

Download Full-text

ChemInform Abstract: The Application of a Structurally Simple, Recyclable, and Large-Scale L-Prolinamide Catalyst for Asymmetric Aldol Reactions.

ChemInform ◽

10.1002/chin.201451022 ◽

2014 ◽

Vol 45 (51) ◽

pp. no-no

Author(s):

Zhi Guan ◽

Yuan Luo ◽

Bao-Qiang Zhang ◽

Krystal Heinen ◽

Da-Cheng Yang ◽

...

Keyword(s):

Large Scale ◽

Aldol Reactions ◽

Asymmetric Aldol

Download Full-text

(S)-5-prolylamide-triazole Organocatalyst for Direct Asymmetric Aldol Reactions

Current Organic Chemistry ◽

10.2174/1385272811317140011 ◽

2013 ◽

Vol 17 (14) ◽

pp. 1563-1568 ◽

Cited By ~ 4

Author(s):

Ling Liu ◽

Min-Na Gao ◽

Yang Li ◽

Zhen Li ◽

Liping Song ◽

...

Keyword(s):

Aldol Reactions ◽

Asymmetric Aldol

Download Full-text

ChemInform Abstract: Organocatalytic Asymmetric Aldol Reactions Mediated by a Cysteine-Derived Prolinamide.

ChemInform ◽

10.1002/chin.200848067 ◽

2008 ◽

Vol 39 (48) ◽

Author(s):

Ricardo S. Schwab ◽

Fabio Z. Galetto ◽

Juliano B. Azeredo ◽

Antonio L. Braga ◽

Diogo S. Luedtke ◽

...

Keyword(s):

Aldol Reactions ◽

Asymmetric Aldol

Download Full-text

Synthesis and evaluation of (S)-proline-containing dipeptidic organocatalysts bound to MBHA resin in asymmetric aldol reactions

Tetrahedron Letters ◽

10.1016/j.tetlet.2015.09.062 ◽

2015 ◽

Vol 56 (44) ◽

pp. 6047-6051 ◽

Cited By ~ 13

Author(s):

Elizabeth Machuca ◽

Giovanna Granados ◽

Bruno Hinojosa ◽

Eusebio Juaristi

Keyword(s):

Aldol Reactions ◽

Asymmetric Aldol

Download Full-text

Intramolecular hydrogen bonding guides a cationic amphiphilic organocatalyst to highly stereoselective aldol reactions in water

RSC Advances ◽

10.1039/c5ra12135c ◽

2015 ◽

Vol 5 (77) ◽

pp. 62331-62335 ◽

Cited By ~ 10

Author(s):

Ángel M. Valdivielso ◽

Alba Catot ◽

Ignacio Alfonso ◽

Ciril Jimeno

Keyword(s):

Hydrogen Bonding ◽

Intramolecular Hydrogen Bonding ◽

Structural Motif ◽

Aldol Reactions ◽

Asymmetric Aldol ◽

Neutral Ph ◽

Intramolecular Hydrogen

A novel amphiphilic acylguanidine organocatalyst using intramolecular hydrogen bonding as a key structural motif is efficient for asymmetric aldol reactions of ketones in water at neutral pH.

Download Full-text