70404-04-5Relevant academic research and scientific papers
SYNTHETIC METHOD OF EPOGYMNOLACTAM AND INTERMEDIATE THEREOF
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, (2019/05/18)
PROBLEM TO BE SOLVED: To provide a synthetic method of an epogymnolactam and an α,β-unsaturated-γ-lactone derivative, which is simple to operate and is more efficient than the conventional synthetic method. SOLUTION: The synthetic method comprises: subjec
A facile synthesis of γ-butenolides via cyclization of 3-alkenoic acids with dimethyl sulfoxide and oxalyl bromide
Ding, Rui,Liu, Yongguo,Liu, Lei,Li, Huimin,Tao, Sichen,Sun, Baoguo,Tian, Hongyu
supporting information, p. 3001 - 3007 (2019/08/26)
The combination of dimethyl sulfoxide and oxalyl bromide was used to accomplish the cyclization of 3-alkenoic acids with the aid of a base to afford γ-butenolides, in which bromodimethylsulfonium salt generated in situ was proposed to serve as a Br+ source.
Borane-Catalyzed Reductive α-Silylation of Conjugated Esters and Amides Leaving Carbonyl Groups Intact
Kim, Youngchan,Chang, Sukbok
supporting information, p. 218 - 222 (2016/01/25)
Described herein is the development of the B(C6F5)3-catalyzed hydrosilylation of α,β-unsaturated esters and amides to afford synthetically valuable α-silyl carbonyl products. The α-silylation occurs chemoselectively, thus leaving the labile carbonyl groups intact. The reaction features a broad scope of both acyclic and cyclic substrates, and the synthetic utility of the obtained α-silyl carbonyl products is also demonstrated. Mechanistic studies revealed two operative steps: fast 1,4-hydrosilylation of conjugated carbonyls and then slow silyl group migration of a silyl ether intermediate.
Convenient synthesis of α,β-unsaturated γ-butyrolactones and γ-butyrolactams via decarboxylative iodination of paraconic acids and β-carboxyl-γ-butyrolactams using 1,3-diiodo-5,5-dimethylhydantoin
Phae-Nok, Supasorn,Kuhakarn, Chutima,Pohmakotr, Manat,Reutrakul, Vichai,Soorukram, Darunee
, p. 11087 - 11095 (2015/11/25)
A convenient synthetic approach to α,β-unsaturated γ-butyrolactones and α,β-unsaturated γ-butyrolactams is developed. The reaction proceeds via decarboxylative iodination of paraconic acids and β-carboxyl-γ-butyrolactams, employing 1,3-diiodo-5,5-dimethylhydantoin (DIH) under irradiation, followed by dehydroiodination of β-iodo-γ-butyrolactones and γ-butyrolactams providing good yields of α,β-unsaturated γ-butyrolactones and γ-butyrolactams, which are synthetically useful building blocks in organic synthesis.
Enantioselective redox-neutral Rh-catalyzed coupling of terminal alkynes with carboxylic acids toward branched allylic esters
Koschker, Philipp,K?hny, Matthias,Breit, Bernhard
, p. 3131 - 3137 (2015/05/20)
We report on the first enantioselective variant of the atom-economic and redox-neutral coupling of carboxylic acids with terminal alkynes under rhodium catalysis utilizing the chiral, bidentate (R,R)-Cp-DIOP ligand. This represents the first example of this convenient asymmetric access to valuable branched allylic esters. The utility of this methodology is demonstrated by both a reaction performed on large scale and a short three-step synthesis of two naturally occurring γ-butyrolactones. A stereochemical model explaining the observed absolute configuration of the products based on DFT calculations is given.
Organocatalytic sequential α-aminoxylation and cis-Wittig olefination of aldehydes: Synthesis of enantiopure γ-butenolides
Devalankar, Dattatray A.,Chouthaiwale, Pandurang V.,Sudalai, Arumugam
experimental part, p. 240 - 244 (2012/06/04)
A short route to enantiopure γ-butenolides (up to 99% ee) has been developed from readily available starting materials. The strategy involves a sequential organocatalytic α-aminoxylation followed by cis-Wittig olefination of aldehydes. The utility of this protocol has been demonstrated in the asymmetric synthesis of trans-(+)-cognac lactone with high enantiomeric purity.
First example of hydrolytic kinetic resolution of acrylate of secondary alcohols by lipase Amano AK
Bora, Pranjal P.,Bez, Ghanashyam,Anal, Jasha Momo H.
experimental part, p. 270 - 275 (2012/07/03)
Lipase Amano AK is found to be extremely efficient catalyst for hydrolytic kinetic resolution of acrylates of secondary alcohols in aqueous phosphate buffer at pH 7.0. Both aliphatic and benzylic secondary alcohols show good to excellent E values.
Catalytic enantioselective synthesis of naturally occurring butenolides via hetero -allylic alkylation and ring closing metathesis
Mao, Bin,Geurts, Koen,Fananas-Mastral, Martin,Van Zijl, Anthoni W.,Fletcher, Stephen P.,Minnaard, Adriaan J.,Feringa, Ben L.
supporting information; experimental part, p. 948 - 951 (2011/04/23)
An efficient catalytic asymmetric synthesis of chiral γ-butenolides was developed based on the hetero-allylic asymmetric alkylation (h-AAA) in combination with ring closing metathesis (RCM). The synthetic potential of the h-AAA-RCM protocol was illustrated with the facile synthesis of (-)-whiskey lactone, (-)-cognac lactone, (-)-nephrosteranic acid, and (-)-roccellaric acid.(Figure Presented)
Asymmetric olefin isomerization of butenolides via proton transfer catalysis by an organic molecule
Wu, Yongwei,Singh, Ravi P.,Deng, Li
supporting information; scheme or table, p. 12458 - 12461 (2011/10/09)
An unprecedented enantioselective and general olefin isomerization was realized via biomimetic proton transfer catalysis with a new chiral organic catalyst. A broad range of mono- and disubstituted β,γ-unsaturated butenolides were transformed into the corresponding chiral α,β- unsaturated butenolides in high enantioselectivity and yield in the presence of as low as 0.5 mol % catalyst. Mechanistic studies have revealed the protonation as the rate-determining step.
Convenient synthesis of 5-alkylfuran-2(5H)-ones
Ma, Jie,Wang, Si Hong,Yin, Yan Bing
, p. 3026 - 3031 (2011/08/22)
A convenient synthesis of 5-alkylfuran-2(5H)-ones are described starting from 3-nitropropanoate and aldehydes, promoted by neutral alumina, in 35-60% overall yields, via a condensation-lactonization-elimination pathway. Copyright
