65051-84-5Relevant articles and documents
Synthesis of Functionalized α-Vinyl Aldehydes from Enaminones
Chen, Jie,Guo, Pan,Zhang, Jianguo,Rong, Jiaxin,Sun, Wangbin,Jiang, Yaojia,Loh, Teck-Peng
supporting information, p. 12674 - 12679 (2019/08/07)
An efficient RhII-catalyzed synthesis of functionalized α-vinyl aldehydes with high E/Z stereoselectivity was developed. The reaction mediates the cyclopropanation of enaminones with vinyl carbenoids that are generated from cyclopropenes in situ to give the aminocyclopropane intermediates. Selective C?C bond cleavage of the cyclopropane intermediates leads to formation of α-vinyl aldehyde derivatives with high E/Z selectivity. This method proceeds at room temperature under very mild reaction conditions and works with a broad substrate scope.
Tandem Hydroalumination/Cu-Catalyzed Asymmetric Vinyl Metalation as a New Access to Enantioenriched Vinylcyclopropane Derivatives
Müller, Daniel S.,Werner, Veronika,Akyol, Sema,Schmalz, Hans-Günther,Marek, Ilan
supporting information, p. 3970 - 3973 (2017/08/14)
Herein, we report the first enantio- and diastereoselective addition of stereodefined vinyl organometallic reagents to cyclopropenes. The operationally simple tandem hydroalumination and copper-catalyzed vinylmetalation allows for the unique access of a diverse set of enantioenriched vinylcyclopropane derivatives.
Asymmetric Copper-Catalyzed Carbozincation of Cyclopropenes en Route to the Formation of Diastereo- and Enantiomerically Enriched Polysubstituted Cyclopropanes
Müller, Daniel S.,Marek, Ilan
supporting information, p. 15414 - 15417 (2015/12/26)
The enantioselective synthesis of cyclopropylzinc reagents has been achieved via a copper-catalyzed carbozincation of 3,3-disubstituted cyclopropenes with diorganozinc reagents. The obtained organozinc compounds can be easily functionalized with a broad range of electrophiles, including palladium-catalyzed cross-couplings, affording highly substituted cyclopropanes. The operationally simple procedure using very low quantities of a commercially available and inexpensive copper catalyst provides a new tool for the synthesis of highly enantioenriched cyclopropanes as single diastereoisomers.