30336-14-2Relevant academic research and scientific papers
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.
Asymmetric olefin isomerization of butenolides via proton transfer catalysis by an organic molecule
Wu, Yongwei,Singh, Ravi P.,Deng, Li
, 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
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)
Catalytic use of selenium electrophiles in cyclizations
Browne, Danielle M.,Niyomura, Osamu,Wirth, Thomas
, p. 3169 - 3172 (2008/02/10)
A new and convenient one-pot method for a catalytic addition-elimination reaction using selenium electrophiles has been developed. In the presence of 5 mol % diphenyl diselenide, [bis(trifluoroacetoxy)iodo]benzene in acetonitrile converted a range of (E)-3-butenoic acids into the corresponding butenolides in good yields.
One-pot synthesis of 5-Alkylfuran-2(5H)-ones
Ma, Jie,Wang, Si Hong,Guan, Rong Tian
, p. 1229 - 1233 (2007/10/03)
5-Alkylfuran-2(5H)-ones can be efficiently obtained using a one-pot approach, starting from methyl 3-nitropropanoate and aldehydes, in ethyl acetate, with Amberlyst A-21 as catalyst, in 60-90% overall yield. Copyright Taylor & Francis Group, LLC.
Stereochemical Dependence of Base-Catalyzed Cleavage of Cyclic Peroxy Ketals
Snider, Barry B.,Shi, Zhongping,O'Neil, Steven V.,Kreutter, Kevin D.,Arakaki, Tracy L.
, p. 1726 - 1729 (2007/10/02)
Base-catalyzed decomposition of cyclic peroxy ketals 1c, 2c, 14, and 16 shows a strong stereochemical dependence.Isomers 2c and 16 with a pseudoequatorial hydrogen undergo a fast antiperiplanar E2 elimination to afford ene diones 4 and 17 that react further.Ester 1c, with a pseudoaxial hydrogen and a pseudoequatorial acetate side chain, reacts slowly to form the enolate, which undergoes an SN2 reaction to give epoxide 3.Peroxy ketals 14 and 15 are stable in base.Peroxy acetals 19 and 20 undergo a faster E2 elimination with loss of the pseudoequatorial acetal proton to provide alkoxide ester 21 that reacts further.
The Synthesis of (Z)-Penta-2,4-dien-1-ol and Substituted (E)-Pentadienols by the Stereochemically Controlled Horner-Wittig Reaction
Brown, Paul S.,Greeves, Nicholas,McElroy, Andrew B.,Warren, Stuart
, p. 1485 - 1492 (2007/10/02)
Acylation of Ph2P(O)Me with a lactone gives a Horner-Wittig intermediate with a Z-double bond protected as a Diels-Alder adduct with furan and hence (Z)-penta-2,4-dien-1-ol.Substituted (E)-penta-2,4-dien-1-ols are available by a more general route involving addition of enals to phosphine oxides, a regiochemically controlled allylic alcohol transposition, and a Horner-Wittig reaction.The geometry of only one double bond can be controlled.
