62222-04-2Relevant articles and documents
Electrophile-Dependent Alkylations of Lithiated 4-Alkoxyalk-4-enenitriles
Pitta, Bhaskar R.,Steward, Omar W.,Fleming, Fraser F.
, p. 2753 - 2762 (2018/03/13)
Alkylations of acyclic, lithiated 4-alkoxyalk-4-enenitriles are highly diastereoselective with an unusual electrophile-dependent preference. Alkyl halides, sulfur, chlorine, and acyl cyanide electrophiles intercept a series of lithiated 4-alkoxyalk-4-enenitriles to install contiguous tertiary-quaternary stereocenters with high diastereoselectivity, whereas acylations with ester and carbonate electrophiles are modestly selective. The diastereoselectivity is consistent with electrophilic attack on the most accessible face of the lithated nitrile for most electrophiles except ester and carbonate electrophiles, which likely precoordinate the lithiated nitrile before acylation. Intercepting the lithiated 4-alkoxyalk-4-enenitriles with a range of electrophiles provide insight into the criteria for otherwise challenging diastereoselective alkylations and acylations of acyclic nitriles.
Chiral primary amine catalyzed asymmetric epoxidation of α-substituted acroleins
Li, Jiuyuan,Fu, Niankai,Zhang, Long,Zhou, Pengxin,Luo, Sanzhong,Cheng, Jin-Pei
supporting information; experimental part, p. 6840 - 6849 (2011/03/19)
1,1-Disubstituted terminal alkenes remain challenging substrates in asymmetric epoxidation reactions. In this study, chiral primary amines are shown to catalyze the asymmetric epoxidation of α-substituted acroleins, a versatile type of 1,1-disubstituted t
Mild organocatalytic α-methylenation of aldehydes
Erkkil?, Anniina,Pihko, Petri M.
, p. 2538 - 2541 (2007/10/03)
A rapid and extremely convenient method for α-methylenation of aldehydes with aqueous formaldehyde is described. Two optimal catalytic systems are presented that allow short reaction times and afford the functionalized products in good to excellent yields (up to 99%) and chemoselectivity.
