92803-34-4Relevant academic research and scientific papers
A stereoselective synthesis of cis-alkenenitriles through reformatsky-Peterson reaction
Palomo, Claudio,Aizpurua, Jesus M.,Aurrekoetxea, Natalia
, p. 2209 - 2210 (1990)
A new procedure for the preparation of alkenenitriles from trimethylsilylchloroacetonitrile and carbonyl compounds promoted by zinc is described.
E- and Z-, di- and tri-substituted alkenyl nitriles through catalytic cross-metathesis
Mu, Yucheng,Nguyen, Thach T.,Koh, Ming Joo,Schrock, Richard R.,Hoveyda, Amir H.
, p. 478 - 487 (2019/04/08)
Nitriles are found in many bioactive compounds, and are among the most versatile functional groups in organic chemistry. Despite many notable recent advances, however, there are no approaches that may be used for the preparation of di- or tri-substituted alkenyl nitriles. Related approaches that are broad in scope and can deliver the desired products in high stereoisomeric purity are especially scarce. Here, we describe the development of several efficient catalytic cross-metathesis strategies, which provide direct access to a considerable range of Z- or E-di-substituted cyano-substituted alkenes or their corresponding tri-substituted variants. Depending on the reaction type, a molybdenum-based monoaryloxide pyrrolide or chloride (MAC) complex may be the optimal choice. The utility of the approach, enhanced by an easy to apply protocol for utilization of substrates bearing an alcohol or a carboxylic acid moiety, is highlighted in the context of applications to the synthesis of biologically active compounds.
A facile, one-pot synthesis of β-substituted (Z)-acrylonitriles utilizing an α-diaminoboryl carbanion
Tomioka, Takashi,Takahashi, Yusuke,Vaughan, Trey G.,Yanase, Takayoshi
supporting information; experimental part, p. 2171 - 2173 (2010/07/08)
A simple three-step single-pot procedure for Z-stereoselective synthesis of β-monosubstituted acrylonitriles has been established. The reaction involves olefination of aldehydes with an in situ generated α-diaminoboryl carbanion species. Various aromatic and aliphatic aldehydes were smoothly converted into the corresponding (Z)-olefin products (up to 96:4 ratio) in good yields (80-98%).
Highly (Z)-selective synthesis of β-monosubstituted α,β-unsaturated cyanides using the peterson reaction
Kojima, Satoshi,Fukuzaki, Tomohide,Yamakawa, Atsushi,Murai, Yutaka
, p. 3917 - 3920 (2007/10/03)
(Chemical Equation Presented) The Peterson reaction between (t-BuO)Ph 2SiCH2CN and various aldehydes furnishes the corresponding β-monosubstituted α,β-unsaturated cyanides with high Z selectivity (Z:E = 92:8 to >98:2).
Highly Z-selective synthesis of disubstituted α, β-unsaturated cyanides and amides using 10-P-5 wittig type reagents
Kojima, Satoshi,Kawaguchi, Kazuhiro,Matsukawa, Shiro,Uchida, Keiichiro,Akiba, Kin-ya
, p. 170 - 171 (2007/10/03)
Phosphoranes (10-P-5) bearing cyanomethyl, acetamide, and N, N-dimethylacetamide groups were examined for Wittig type reactions. All three reacted to give the corresponding olefins. The reaction of the cyanomethyl reagent with aldehydes gave α, β-unsatura
