586952-07-0Relevant academic research and scientific papers
A simple procedure for the synthesis of γ-hydroxy-α,β-(E)- alkenoic esters: Formal synthesis of (+)-macrosphelides a and B
Srinivasa Rao,Mukkanti,Srinivasa Reddy,Pal, Manojit,Iqbal, Javed
, p. 2287 - 2290 (2005)
A highly trans-selective conjugate reduction of γ-hydroxy-α, β-alkynoic esters to produce γ-hydroxy-α,β-(E)-alkenoic esters using LiAlH4 is reported. The application of this methodology is demonstrated by a formal synthesis of the potent cell-cell adhesion inhibitors (+)-macrosphelides A and B.
Chemoselective reduction of aldehydes and ketones by potassium diisobutyl-t-butoxy aluminum hydride (PDBBA)
Kim, Joo Yeon,Shin, Won Kyu,Jaladi, Ashok Kumar,An, Duk Keun
, p. 4236 - 4241 (2018/06/30)
t-Butoxy derivatives of DIBALH [lithium diisobutyl-t-butoxyaluminum hydride (LDBBA), sodium diisobutyl-t-butoxyaluminum hydride (SDBBA), and potassium diisobutyl-t-butoxyaluminum hydride (PDBBA)] were examined as chemoselective reducing agents of carbonyl compounds. Among them, PDBBA was found to be the most efficient for the reduction of aldehydes and ketones to the corresponding alcohols in the presence of ester, amide, and nitrile substituents at ambient temperature. In addition, the optimal conditions gave higher chemoselectivity for aldehydes in the presence of ketones.
Ring Expansion of Epoxides under Br?nsted Base Catalysis: Formal [3+2] Cycloaddition of β,γ-Epoxy Esters with Imines Providing 2,4,5-Trisubstituted 1,3-Oxazolidines
Kondoh, Azusa,Odaira, Kenta,Terada, Masahiro
, p. 11240 - 11244 (2016/07/06)
A novel ring-expansion reaction of epoxides under Br?nsted base catalysis was developed. The formal [3+2] cycloaddition reaction of β,γ-epoxy esters with imines proceeds in the presence of triazabicyclodecene (TBD) as a superior Br?nsted base catalyst to afford 2,4,5-trisubstituted 1,3-oxazolidines in a highly diastereoselective manner. This reaction involves the ring opening of the epoxides with the aid of the Br?nsted base catalyst to generate α,β-unsaturated esters having an alkoxide at the allylic position, which would formally serve as a synthetic equivalent of the 1,3-dipole, followed by a cycloaddition reaction with imines in a stepwise fashion. This methodology enables the facile synthesis of enantioenriched 1,3-oxazolidines from easily accessible enantioenriched epoxides.
Gold-catalyzed [3+2] cycloaddition/hydrolytic Michael addition/retro-aldol reactions of propargylic esters tethered to cyclohexadienones
Cai, Shunyou,Liu, Zheng,Zhang, Weibin,Zhao, Xinyang,Wang, David Zhigang
supporting information; experimental part, p. 11133 - 11137 (2012/02/02)
A golden dance! A series of symmetric and nonsymmetric propargylic esters tethered to cyclohexadienones were found to undergo the title reaction sequence under mild reaction conditions through gold catalysis. The product cyclohexenones or cyclohexanones having a γ-quaternary center arise from simultaneous multiatom transpositions with complete stereochemical control. Copyright
Diastereoselective synthesis of γ-hydroxy α,β-epoxyesters and their conversion into β-hydroxy α-sulfenyl γ-butyrolactones
Rodríguez, Santiago,Kneeteman, María,Izquierdo, Javier,López, Irakusne,González, Florenci?V.,Peris, Gabriel
, p. 11112 - 11123 (2007/10/03)
The diastereoselectivity of the nucleophilic epoxidation of γ-hydroxy-α,β-unsaturated esters has been studied. The γ-hydroxy-α,β-unsaturated esters were obtained through treatment of ethyl (E)-4-oxo-2-butenoate with the corresponding Grignard reagent and
Stereoselective synthesis of trans-4,5-disubstituted oxazolidin-2-ones by intramolecular conjugate addition of N-p-toluenesulfonyl carbamates
Ciclosi, Marco,Fava, Cristiana,Galeazzi, Roberta,Orena, Mario,Sepúlveda-Arques, José,González-Rosende, Maria Eugenia
, p. 1173 - 1183 (2007/10/03)
p-Toluenesulfonyl carbamates (2a-d) were prepared starting from allylic alcohols (3), in which the double bond is conjugated with an electron withdrawing group. In the presence of a catalytic amount of DBU, an intramolecular cyclisation occurred, leading
Truly catalytic Meerwein-Ponndorf-Verley (MPV) reduction
Akamanchi, Krishnacharya G.,Noorani, Varalakshmy R.
, p. 5085 - 5088 (2007/10/02)
A truly catalytic version of MPV reduction system has been developed. Herein p-nitrobenzaldehyde has been completely reduced at room temperature within 15 minutes using catalytic amounts of aluminium isopropoxide modified by trifluoroacetic acid and just one mole equivalent of isopropyl alcohol as external hydride source.
Reductive Cyclization of Ketoesters Utilizing Sodium Cyanoborohydride: Synthesis of γ- and δ-Lactones
Podraza, Kenneth F.
, p. 293 - 295 (2007/10/02)
A new one pot procedure to synthesize γ- and δ-lactones, in a 76-84percent yield, is accomplished by the reductive cyclization of 1,4- and 1,5-ketoesters, utilizing sodium cyanoborohydride.The procedure is generally applicable to a wide variety of ketoesters with the exception of the ethyl ester of alkyl 1,5-ketoesters and α,β-unsaturated 1,4- and 1,5-ketoesters.
