295328-86-8Relevant articles and documents
Enantioselective Stetter Reactions Catalyzed by Bis(amino)cyclopropenylidenes: Important Role for Water as an Additive
Rezazadeh Khalkhali, Mehran,Wilde, Myron M. D.,Gravel, Michel
, p. 155 - 159 (2021/01/09)
The first highly enantioselective intermolecular Stetter reaction using simple enones is reported. A series of novel chiral BAC structures were designed and prepared. They were tested in the Stetter reaction with simple aldehydes and enones. The products were generated in excellent yields and enantioselectivities (up to 94% ee). Surprisingly, a substoichiometric amount of water was crucial to obtain high enantioselectivities. Chiral BACs were also shown to catalyze 1,6-conjugate addition reactions with paraquinone methides enantioselectively.
A general, enantioselective synthesis of N-alkyl terminal aziridines and C2-functionalized azetidines via organocatalysis
Senter, Timothy J.,O'Reilly, Matthew C.,Chong, Katherine M.,Sulikowski, Gary A.,Lindsley, Craig W.
, p. 1276 - 1279 (2015/03/04)
A short, high-yielding protocol involving the enantioselective α-chlorination of aldehydes has been developed for the enantioselective synthesis of C2-functionalized aziridines and N-alkyl terminal azetidines from a common intermediate. This methodology allows for the rapid preparation of functionalized aziridines in 50-73% overall yields and 88-94% ee, and azetidines in 22-32% overall yields and 84-92% ee. Moreover, we developed a scalable and cost-effective route to the key organocatalyst (54% overall yield, >95% dr).
Efficient preparation of optically pure C2-symmetrical cyclic amines for chiral auxiliary
Sato, Mitsuo,Gunji, Yasuhiko,Ikeno, Taketo,Yamada, Tohru
, p. 1434 - 1438 (2007/10/03)
Optically pure C2-symmetrical amines were efficiently synthesized from the corresponding diols obtained from the enantioselective borohydride reduction of the diketones catalyzed by the optically active β-ketoiminato cobalt(II) complex.
