87995-21-9Relevant academic research and scientific papers
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.
Reinvestigation of the fluoride-triggered condensation of allyltrimethylsilane with cinnamonitrile: 'Abnormal Sakurai' and sequential 'abnormal Sakurai'-Michael-Thorpe Ziegler side reactions
Keller, Laurent,Dumas, Fran?oise,Pizzonero, Mathieu,D'Angelo, Jean,Morgant, Georges,Nguyen-Huy, Dung
, p. 3225 - 3228 (2007/10/03)
Together with the expected 1,4-adduct, three by-products are generated in the fluoride-triggered condensation of allyltrimethylsilane with cinnamonitrile: the 1,3 adduct, an acyclic dinitrile and a cyclopentenaminonitrile issuing, respectively, from 'abnormal Sakurai', 'abnormal Sakurai'-Michael and 'abnormal Sakurai'-Michael-Thorpe Ziegler side reactions.
CHEMOSELECTIVITY IN THE CONJUGATE ADDITION OF ALLYLSILANE TO MICHAEL ACCEPTORS
Majetich, George,Casares, Ada M.,Chapman, D.,Behnke, M.
, p. 1909 - 1912 (2007/10/02)
The allylic carbanion species generated by treatment of allylsilane with fluoride ion undergoes highly chemoselective conjugate addition to a series of Michael acceptors for which alternative known allylation procedures proved less general.
