ChemInform Abstract: Enantioselective Organocatalytic Conjugate Reduction of β-Azole-Containing α,β-Unsaturated Aldehydes.

ChemInform ◽  
2009 ◽  
Vol 40 (46) ◽  
Author(s):  
Thomas J. Hoffman ◽  
Jyotirmayee Dash ◽  
James H. Rigby ◽  
Stellios Arseniyadis ◽  
Janine Cossy
Keyword(s):  
Unsaturated Aldehydes ◽  
Conjugate Reduction

A Metal-Free Transfer Hydrogenation: Organocatalytic Conjugate Reduction of ?,?-Unsaturated Aldehydes.

ChemInform ◽  
2005 ◽  
Vol 36 (16) ◽  
Author(s):  
Jung Woon Yang ◽  
Maria T. Hechavarria Fonseca ◽  
Benjamin List
Keyword(s):  
Transfer Hydrogenation ◽  
Metal Free ◽  
Unsaturated Aldehydes ◽  
Conjugate Reduction

Conjugate Reduction of α,β-Unsaturated Aldehydes with Rhodium(bis­oxazolinylphenyl) Catalysts

Synlett ◽  
2006 ◽  
Vol 2006 (19) ◽  
pp. 3343-3345 ◽  
Author(s):  
Hisao Nishiyama ◽  
Yoshinori Kanazawa
Keyword(s):  
Unsaturated Aldehydes ◽  
Conjugate Reduction

Enantioselective Organocatalytic Conjugate Reduction of β-Azole-Containing α,β-Unsaturated Aldehydes

2009 ◽  
Vol 11 (13) ◽  
pp. 2756-2759 ◽  
Author(s):  
Thomas J. Hoffman ◽  
Jyotirmayee Dash ◽  
James H. Rigby ◽  
Stellios Arseniyadis ◽  
Janine Cossy
Keyword(s):  
Unsaturated Aldehydes ◽  
Conjugate Reduction

THE TOXICITY AND DETOXIFICATION OF α, β-UNSATURATED ALDEHYDES

1999 ◽  
Vol 14 (supplement) ◽  
pp. 74-75
Author(s):  
Akira HIRATSUKA ◽  
Kenichiro HIROSE ◽  
Hiroaki NAKANO ◽  
Tadashi WATABE
Keyword(s):  
Unsaturated Aldehydes

Asymmetric Peroxidation of α,β-Unsaturated Aldehydes under Diarylprolinol Ether Catalysis

2017 ◽  
Vol 21 (19) ◽  
Author(s):  
K. O'Reilly ◽  
M. K. Gupta ◽  
H. Gandhi ◽  
V. P. Kumar ◽  
T. P. O'Sullivan
Keyword(s):  
Unsaturated Aldehydes

scholarly journals Theoretical Insight into the Reversal of Chemoselectivity in Diels-Alder Reactions of α,β-Unsaturated Aldehydes and Ketones Catalyzed by Brønsted and Lewis Acids

Organics ◽  
2021 ◽  
Vol 2 (1) ◽  
pp. 38-49
Author(s):  
Lakhdar Benhamed ◽  
Sidi Mohamed Mekelleche ◽  
Wafaa Benchouk
Keyword(s):  
Lewis Acids ◽  
Major Product ◽  
Diels Alder ◽  
Unsaturated Ketone ◽  
Unsaturated Aldehydes ◽  
Aldehydes And Ketones ◽  
Theoretical Insight ◽  
Insight Into ◽  
Good Agreement

Experimentally, a reversal of chemoselectivity has been observed in catalyzed Diels–Alder reactions of α,β-unsaturated aldehydes (e.g., (2E)-but-2-enal) and ketones (e.g., 2-hexen-4-one) with cyclopentadiene. Indeed, using the triflimidic Brønsted acid Tf2NH as catalyst, the reaction gave a Diels–Alder adduct derived from α,β-unsaturated ketone as a major product. On the other hand, the use of tris(pentafluorophenyl)borane B(C6F5)3 bulky Lewis acid as catalyst gave mainly the cycloadduct of α,β-unsaturated aldehyde as a major product. Our aim in the present work is to put in evidence the role of the catalyst in the reversal of the chemoselectivity of the catalyzed Diels–Alder reactions of (2E)-but-2-enal and 2-Hexen-4-one with cyclopentadiene. The calculations were performed at the ωB97XD/6-311G(d,p) level of theory and the solvent effects of dichloromethane were taken into account using the PCM solvation model. The obtained results are in good agreement with experimental outcomes.

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