94535-16-7Relevant articles and documents
Direct Synthesis of α-Amino Nitriles from Sulfonamides via Base-Mediated C-H Cyanation
Shi, Shasha,Yang, Xianyu,Tang, Man,Hu, Jiefeng,Loh, Teck-Peng
supporting information, p. 4018 - 4022 (2021/05/26)
Herein, we disclose a transition-metal-free reaction system that enables α-cyanation of sulfonamides through C-H bond cleavage for the preparation of α-amino nitriles, including difficult-to-access all-alkyl α-tertiary scaffolds. More than 50 substrate examples prove a wide functional group tolerance. Additionally, its synthetic practicality is highlighted by gram-scalability and the late-stage modification of natural compounds. Mechanistic experiments suggest that this process involves in situ formation of an imine intermediate via base-promoted elimination of HF.
A simple and convenient synthesis of 2-methoxyestradiol from estrone
Prakasham,Shanker, Karuna,Negi, Arvind S.
scheme or table, p. 467 - 470 (2012/05/19)
A simple and straightforward synthesis of 2-methoxyestradiol have been achieved in nine synthetic steps with 21% of overall yield. Being a convenient process, it can be upscaled to industrial process.
Transition metal-catalyzed intramolecular [4+2] cycloadditions: Mechanistic and synthetic investigations
Wender, Paul A.,Smith, Thomas E.
, p. 1255 - 1275 (2007/10/03)
The nickel-catalyzed intramolecular cycloaddition of dienes with unactivatable alkynes is found to proceed under mild conditions while the corresponding Diels-Alder cycloaddition of the same substrates either fails of occurs only under forcing conditions. The nickel-catalyzed cycloaddition is also shown to occur with retention of stereochemistry and is not significantly influenced by electronic effects. Finally, the catalyzed process is shown to be applicable to the synthesis of angularly substituted bicycles, including the CD ring systems of steroids and vitamin D.
