ChemInform Abstract: Asymmetric Aldol Reactions Between Cyclic Ketones and Benzaldehyde Catalyzed by Chiral Zn2+Complexes of Aminoacyl 1,4,7,10-Tetraazacyclododecane: Effects of Solvent and Additives on the Stereoselectivities of the Aldol Products.

Porcine pancreas lipase type II (PPL II) exhibited unnatural catalytic activity in direct asymmetric aldol reactions between cyclic ketones and aromatic or heteroaromatic aldehydes in acetonitrile in the presence of phosphate buffer. A wide range of substrates was accepted by the enzyme to afford the corresponding aldol products in low to high yields (10 - 98%), with moderate to excellent enantioselectivities (53 - 94% ee, for anti-isomers) and low to moderate diastereoselectivities (48/52 - 87/13 dr, anti/syn). This methodology expands the application of PPL II, and it might be developed into a potentially valuable method for sustainable organic synthesis.

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(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

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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

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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

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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.

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