ChemInform Abstract: MgBr2-Mediated Ionic Diels—Alder Reaction of Acetals of α,β-Unsaturated Aldehydes and Ketones with 1,3-Dienes.

ChemInform ◽  
2008 ◽  
Vol 39 (1) ◽  
Author(s):  
Subhash P. Chavan ◽  
Krishna S. Ethiraj ◽  
Shubhada W. Dantale
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Unsaturated Aldehydes ◽  
Diels Alder Reaction ◽  
Aldehydes And Ketones

Mesoporous Al-containing MCM-41 molecular sieves: highly active catalysts for Diels–Alder reaction of cyclopentadiene with α,β-unsaturated aldehydes

2003 ◽  
Vol 245 (2) ◽  
pp. 353-362 ◽  
Author(s):  
Tsuyoshi Kugita ◽  
Suman K. Jana ◽  
Tomo Owada ◽  
Naoki Hashimoto ◽  
Makoto Onaka ◽  
...  
Keyword(s):  
Molecular Sieves ◽  
Alder Reaction ◽  
Diels Alder ◽  
Unsaturated Aldehydes ◽  
Highly Active ◽  
Diels Alder Reaction ◽  
Mcm 41

Diels–Alder reaction of β-chloro-α,β-unsaturated aldehydes with cyclopentadiene: an experimental and theoretical study

2013 ◽  
Vol 25 (3) ◽  
pp. 799-808 ◽  
Author(s):  
Thouraya M. Barhoumi-Slimi ◽  
K. Essalah ◽  
M. A. K. Sanhoury ◽  
M. Ourévitch ◽  
M. M. El Gaied
Keyword(s):  
Theoretical Study ◽  
Alder Reaction ◽  
Diels Alder ◽  
Unsaturated Aldehydes ◽  
Diels Alder Reaction

1996 Merck Frosst Award Lecture Synthetic adventures along a Rocky Mountain road

1997 ◽  
Vol 75 (9) ◽  
pp. 1163-1171 ◽  
Author(s):  
Brian A. Keay ◽  
Shawn P. Maddaford ◽  
Walter A. Cristofoli ◽  
Neil G. Andersen ◽  
Marco S. Passafaro ◽  
...  
Keyword(s):  
Suzuki Reaction ◽  
Rocky Mountain ◽  
Alder Reaction ◽  
Diels Alder ◽  
One Pot ◽  
Diels Alder Reaction ◽  
Aldehydes And Ketones ◽  
Palladium Catalyzed ◽  
Therapeutic Research

This paper describes the chemistry presented during the Merck Frosst Centre for Therapeutic Research Lecture Award given at the 79th Chemistry in Canada Conference held in St. John's, Newfoundland in June 1996. The first section describes the synthesis of (+)-xestoquinone using an asymmetric palladium-catalyzed polyene cyclization as the key step that creates the C and D rings and the stereogenic centre (68% ee) in one step. Extensions of the work involving an in situ Suzuki reaction are presented. The synthesis of C2-symmetric biaryls and the synthesis of a recently isolated binaphthyl natural product is described using this new method. A new one-pot desilylation–oxidation procedure of silyl ethers is described in detail for the preparation of aldehydes and ketones directly without the need for the isolation of the alcohol intermediate. Finally, a highly diastereoselective (>97%) Diels–Alder reaction is presented using (+)-cis,cis-spiro[4.4]nonane-1,6-diol as a new chiral auxiliary. One of the alcohols is attached to a pivalate, the other to an acrylate, and the Diels–Alder reaction with cyclopentadiene provides only one adduct (by 1H NMR and HPLC) with the endo stereochemistry. Keywords: (+)-xestoquinone, asymmetric palladium-catalyzed polyene cyclization, in situ Suzuki reaction, desilylation–oxidation reaction, spirodiols, chiral auxiliaries.

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