22911-31-5Relevant academic research and scientific papers
Efficient Access to All-Carbon Quaternary and Tertiary α-Functionalized Homoallyl-type Aldehydes from Ketones
Pace, Vittorio,Castoldi, Laura,Mazzeo, Eugenia,Rui, Marta,Langer, Thierry,Holzer, Wolfgang
supporting information, p. 12677 - 12682 (2017/09/08)
β,γ-Unsaturated aldehydes with all-carbon quaternary or tertiary α-centers were rapidly assembled from ketones through a unique synthetic operation consisting of 1) C1 homologation, 2) Lewis acid mediated epoxide–aldehyde isomerization, and 3) electrophilic trapping. The synthetic equivalence of a vinyl oxirane and a β,γ-unsaturated aldehyde is the key concept of this previously undisclosed tactic. Mechanistic studies and labeling experiments suggest that an aldehyde enolate is a crucial intermediate. The homologating carbenoid formation plays a critical role in determining the chemoselectivity.
Radical-mediated diamination of alkenes with phenylhydrazine and azodicarboxylates: Highly diastereoselective synthesis of trans-diamines from cycloalkenes
Zhu, Ming-Kui,Chen, Yu-Chen,Loh, Teck-Peng
supporting information, p. 5250 - 5254 (2013/05/23)
Metal-free synthesis: Diamination of alkenes by using phenylhydrazine and azodicarboxylates could be achieved in a one-pot manner under very mild conditions (see scheme; Boc=tert-butoxycarbonyl). This process works with the assistance of acetic acid by me
