69492-29-1Relevant articles and documents
Trisubstituted Highly Activated Benzo[ d]thiazol-2-yl-sulfone-Containing Olefins as Building Blocks in Organic Synthesis
Baar, Lubomír V.,J.-Y. D. Bon, David,Ková?, Ond?ej,Pospí?il, Ji?í,Roiser, Lukas,Waser, Mario,Zále?ák, Franti?ek
, p. 7192 - 7206 (2020/06/27)
In this paper, we report the formation of highly electrophilic 1,1-deactivated olefins, their use as novel synthetic building blocks, and their transformation to structurally diverse molecular scaffolds. Synthesis of 1,1-deactivated olefins substituted with a BT-sulfonyl group and a carbonyl or nitrile, respectively, consists of unusual Ti(OPri)4-mediated Knoevenagel-type condensation and proceed in good to excellent yields. Generated olefins can be further transformed in a highly stereoselective manner and in good yields to various polyfunctionalized heterocycles and acyclic molecular scaffolds. Overall, the obtained structures are accessed in two to four steps starting from the (mostly) commercially available aldehydes. In addition, the presence of the BT-sulfonyl group in prepared structures allows for further chemoselective functionalization/post-synthetic transformations to provide structurally diverse final compounds.
Primary-amine-catalyzed enantioselective intramolecular aldolizations
Zhou, Jian,Wakchaure, Vijay,Kraft, Philip,List, Benjamin
supporting information; experimental part, p. 7656 - 7658 (2009/04/10)
Aldol cyclodehydration of 4-substituted-2,6-heptanediones leads to enantiomerically enriched 5-substituted-3-methyl-2-cyclohexene-1-ones, which serve as perfume ingredients and valuable synthetic building blocks.Primary amines derived from cinchona alkalo
Effect of InCl3 on the addition of Grignard reagents to α,β-unsaturated carbonyl compounds
Kelly, Brian G.,Gilheany, Declan G.
, p. 887 - 890 (2007/10/03)
Control of 1,2- versus 1,4-addition of organometallic reagents to enones remains a long-standing problem. There is still no satisfactory 1,2-directing agent comparable to the 1,4-directing effect of copper salts. We report that the presence of just 5 mol% indium(III) chloride can significantly alter the amount of 1,2-product formed in these reactions.
