- A robust nickel catalyst for cyanomethylation of aldehydes: Activation of acetonitrile under base-free conditions
-
Nick of time: The nickel cyanomethyl complex 1 catalyzes the room temperature coupling of aldehydes with acetonitrile under base-free conditions. The catalytic system is long-lived and remarkably efficient with high turnover numbers (TONs) and turnover fr
- Chakraborty, Sumit,Patel, Yogi J.,Krause, Jeanette A.,Guan, Hairong
-
supporting information
p. 7523 - 7526
(2013/07/26)
-
- N-Heterocyclic carbene-catalyzed cyanomethylation of aldehydes with TMSAN
-
N-Heterocyclic carbenes (NHCs) have been served as efficient catalysts for cyanomethylation of carbonyl compounds. In the presence of 5 mol % NHC, various aldehydes and 2,2,2-trifluoroacetophenone reacted with trimethylsilylacetonitrile (TMSAN) to give β-hydroxynitriles in moderate to high yields.
- Fan, Ye-Cheng,Du, Guang-Fen,Sun, Wan-Fu,Kang, Wei,He, Lin
-
supporting information; experimental part
p. 2231 - 2233
(2012/05/20)
-
- P(i-PrNCH2CH2)3N as a Lewis base catalyst for the synthesis of β-hydroxynitriles using TMSAN
-
(Equation Presented) Proazaphosphatrane 1a was found to be an efficient catalyst for synthesis of β-hydroxynitriles via the reaction of trimethylsilylacetonitrile (TMSAN) with aldehydes under mild reaction conditions and typically low catalyst loading (ca. 2 mol %). A variety of functional groups were tolerated, and good to excellent product yields were obtained.
- Wadhwa, Kuldeep,Verkade, John G.
-
experimental part
p. 5683 - 5686
(2009/12/06)
-
- Lewis base-catalyzed cyanomethylation of carbonyl compounds with (trimethylsilyl)acetonitrile
-
Catalytic cyanomethylation of various carbonyl compounds with (trimethylsilyl)acetonitrile (TMSCH2CN) in the presence of Lewis bases such as cesium or lithium acetate proceeded smoothly to afford the corresponding cyanomethylated adducts in good yields. Copyright
- Kawano, Yoshikazu,Kaneko, Nobuya,Mukaiyama, Teruaki
-
p. 1508 - 1509
(2007/10/03)
-
- Efficient Lipase-Catalyzed Kinetic Resolution and Dynamic Kinetic Resolution of β-Hydroxy Nitriles. A Route to Useful Precursors for γ-Amino Alcohols
-
An efficient kinetic resolution of racemic β-hydroxy nitriles 1 was performed via Candida antarctica lipase (N-435)-catalyzed transesterification. A variety of racemic alkyl, aryl, and aryloxymethyl substituted β-hydroxy nitriles was efficiently transformed to the corresponding enantiomerically pure acetates (ee > 99% and conversion = 50%) with E values from 40 to > 1000. The combination of the enzymatic kinetic resolution with a ruthenium-catalyzed alcohol racemization led to a dynamic kinetic resolution (ee's up to 99%, yields up to 85%).
- Pàmies, Oscar,B?ckvall, Jan-E.
-
p. 726 - 731
(2007/10/03)
-
- Synthesis of β-Hydroxy Nitriles via Indium-Induced Coupling of Bromoacetonitrile with Carbonyl Compounds
-
The organoindium reagent, derived from indium metal and bromoacetonitrile, reacted with carbonyl compounds in the presence of chlorotrimethylsilane to give, after hydrolysis, β-hydroxy nitriles.The coupling proceeded with high chemoselectivity, though the diastereoselectivity was low.
- Araki, Shuki,Yamada, Masafumi,Butsugan, Yasuo
-
p. 1126 - 1129
(2007/10/02)
-
- STEREOSELECTIVE ALDOL CONDENSATIONS OF ORGANOTIN REAGENTS WITH ALDEHYDES
-
The reaction of the enolstannanes of cyclohexanone or propiophenone with various aldehydes under kinetic control (-78 deg C) gave predominately the threo aldols, diastereoselectivity as high as 95:5 being achived.At higher temperatures (+45 deg C) predominate erythro selectivity was observed.The enolstannane of propiophenone exists as an equilibrium mixture of O-Sn (probably the E-isomer) and C-Sn derivatives.Reaction at -78 deg C takes place rapidly with the O-Sn enolate, further reaction requiring isomerization of the C-Sn to the O-Sn enolate.The Pd catalyzed condensation of cyanomethyltributyltin with reactive aldehydes, such as nitrobenzaldehydes, took place at ambient temperatures in polar solvents to give high yields of condensation products.No reaction occured with aldehydes such as benzaldehyde.Only low stereoselectivity (10-34percent ee) was observed when (-)DIOP or (-)BPPM were utilized as chiral phosphine ligands.
- Labadie, Sharada S.,Stille, J. K.
-
p. 2329 - 2336
(2007/10/02)
-
- AN ALDOL-TYPE REACTION OF ACETONITRILES USING DIALKYLBORYL TRIFLATE
-
Acetonitriles and benzaldehydes react in the presence of dialkyl boryl triflate and diisopropylethylamine in dichloromethane to give the corresponding aldol-type products in good yields under mild conditions.
- Hamana, Hiroshi,Sugasawa, Tsutomu
-
p. 1401 - 1404
(2007/10/02)
-