476167-72-3Relevant academic research and scientific papers
Synthesis of β-Lactams via Enantioselective Allylation of Anilines with Morita-Baylis-Hillman Carbonates
Krieck, Sven,Lange, Markus,Schüler, Philipp,Vilotijevic, Ivan,Westerhausen, Matthias,Zi, You
, p. 575 - 580 (2020/03/27)
Enantioenriched β-lactams are accessed via enantioselective allylation of anilines with Morita-Baylis-Hillman carbonates followed by a base-promoted cyclization. The resulting 3-methyleneazetidin-2-ones are amenable to diastereoselective functionalization
Accelerated amination of baylis-hillman acetates under ultrasound irradiation
Ge, Shao-Qin,Hua, Yun-Yu,Xia, Min
experimental part, p. 1954 - 1962 (2010/09/09)
The amination of the Baylis-Hillman acetates with primary amines can be dramatically promoted with improved yields and shortened reaction time under ultrasound irradiation. The selected aromatic, heteroaromatic, and aliphatic amines were investigated as t
Chemical transformation of Baylis-Hillman adducts: The reaction of methyl 3-arylamino-2-methylene-3-phenylpropanoates in polyphosphoric acid
Lee, Chang Gon,Lee, Ka Young,Lee, Sangku,Kim, Jae Nyoung
, p. 1493 - 1499 (2007/10/03)
We synthesized some interesting compounds including 3-benzylidene-3,4- dihydro-1H-quinolin-2-one, 3-benzylquinolin-2-ol, 4-amino-2-benzylideneindan-1- one, and 1-amino-9a,10-dihydro-4bH-indeno[1,2-a]inden-9-one skeletons starting from Baylis-Hillman adducts.
Palladium(0)-catalyzed regioselective synthesis of α-dehydro-β-amino esters from amines and allyl acetates: Synthesis of a α-dehydro-β-amino acid derived cyclic peptide as a constrained β-turn mimic
Rajesh,Banerji, Biswadip,Iqbal, Javed
, p. 7852 - 7857 (2007/10/03)
Acetates derived from the adducts of the Baylis-Hillman reaction can be reacted in a regioselective manner with amines in the presence of palladium(0) catalyst to afford α-dehydro-β-amino esters (2 and 3) in good yields. The regioselectivity of the reaction can be controlled by temperature and reaction medium leading to the synthesis of regioisomers 2 or 3. The α-dehydro-β-amino acid 3 is a turn inducer, and the dipeptides 6 derived from it show the presence of an eight-membered intramolecular hydrogen bond. Also, cobalt(II) chloride catalyzes the cleavage of epoxy peptides with α-dehydro-β-amino acid derivative 3b to afford the corresponding dipeptide derivatives 8, which exhibit an intramolecular hydrogen bond and thus mimic a β-turn. This intramolecular hydrogen bonding preorganizes the corresponding diallylated peptide 8c for cyclization via ring-closing metathesis to afford the cyclic peptide 9 as a constrained mimic of a β-turn.
