103547-98-4Relevant articles and documents
An efficient synthesis of α-methylene-β-butyrolactones from Baylis-Hillman adducts via an In-mediated Barbier reaction and stereoselective lactonization under MeSO2Cl/Et3N conditions
Park, Bo Ram,Kim, Ko Hoon,Kim, Jae Nyoung
, p. 6568 - 6571 (2010)
An efficient synthesis of trans-α-methylene-β-butyrolactones is disclosed from syn-homoallylic alcohols via the intramolecular mesylate displacement reaction promoted by nearby ester group under the influence of MsCl/Et3N. syn-Homoallylic alcoh
Stereoselective radical addition to α-methylenebutyrolactones by indirect electroreduction catalyzed by a nickel(II) complex
Ozaki, Shigeko,Matsui, Eiki,Ohmori, Hidenobu
, p. 198 - 201 (1997)
The addition of butyl radicals to β- and/or γ-disubstituted α- methylenebutyrolactones by a nickel(II) complex-catalyzed indirect electroreduction using equimolar amounts of butyl iodides and α- methylenebutyrolactones provides cis-(C-α): (C-β)-trisubstit
Enantioselective Dreiding-Schmidt reactions: Asymmetric synthesis and analysis of α-methylene-γ-butyrolactones
Csuk, Rene,Schroeder, Christina,Hutter, Sonja,Mohr, Kristina
, p. 1411 - 1429 (1997)
The zinc/silver-graphite mediated Dreiding-Schmidt reactions between aldehydes and the 2-bromomethyl-acrylate derived sultamamides (+)/(-)-28 or (+)/(-)-30 gave the corresponding substituted α-methylene-γ-butyrolactones with ee's up to 90%. Enantiomerically pure compounds were obtained by semipreparative HPLC using a chiral stationary phase.
Tailored α-methylene-γ-butyrolactones and their effects on growth suppression in pancreatic carcinoma cells
Ramachandran, P. Veeraraghavan,Pratihar, Debarshi,Nair, Hari Narayanan G.,Walters, Matthew,Smith, Sadie,Yip-Schneider, Michele T.,Wu, Huangbing,Schmidt, C. Max
, p. 6620 - 6623 (2010)
A selected series of racemic α-methylene-γ-butyrolactones (AMGBL) were synthesized via allylboration and screened against three human pancreatic cancer cell lines (Panc-1, MIA PaCa-2, and BxPC-3). This systematic study established a discernible relationsh
Control of stereochemistry: A general synthesis of cis- or trans-β,γ-disubstituted-γ-butyrolactones following Z-crotylboration
Ramachandran, P. Veeraraghavan,Pratihar, Debarshi,Biswas, Debanjan
, p. 3877 - 3879 (2006)
A general and practical procedure for the highly diastereoselective preparation of either the cis- or trans-β,γ-disubstituted-γ- butyrolactones by appropriate choice of Lewis or Bronsted acid catalysts during crotylboration or lactonization is reported. T
Triflic acid-catalyzed additions of 2-alkoxycarbonyl allylboronates to aldehydes. Study of scope and mechanistic investigation of the reaction stereochemistry
Elford, Tim G.,Arimura, Yuichiro,Siu, Hong Yu,Hall, Dennis G.
, p. 1276 - 1284 (2007/10/03)
(Chemical Equation Presented) The substrate scope and the effect of substrate on the observed inversion of stereoselectivity in the triflic acid-catalyzed allylboration reaction between 2-alkoxycarbonyl allylboronates and aldehydes are presented. A mechan
Baylis-Hillman chemistry: synthesis of cis- and trans-α-methylene-γ-lactones
Kabalka, George W.,Venkataiah, Bollu,Chen, Chunlan
, p. 4187 - 4189 (2007/10/03)
syn-Homoallylic alcohols prepared from Baylis-Hillman adducts react with CBr4/PPh3 to give trans-α-methylene-γ-lactones. Notably, the same alcohols yield the cis-α-methylene-γ-lactones in the presence of traces of p-toluenesulfonic a
Lewis acid catalyzed allylboration: Discovery, optimization, and application to the formation of stereogenic quaternary carbon centers
Kennedy, Jason W. J.,Hall, Dennis G.
, p. 4412 - 4428 (2007/10/03)
A full account of the development of the first catalytic manifold for the additions of allylboronates to aldehydes is described. The thermal additions (both diastereospecific and enantioselective) of 2-carboxyester 3,3-disubstituted allylboronates 1 to both aromatic and aliphatic aldehydes give biologically and synthetically important exo-methylene butyrolactones 2 containing a β-quaternary carbon center. Although the thermal reaction requires 14 d at room temperature to reach completion, the presence of certain metal salts allows for a 12-16 h reaction while preserving the dia-stereospecificity observed in the uncatalyzed process. Preliminary mechanistic studies on the origin of the catalytic effect are described as well as stereoselective transformations of lactones 2 into cyclic and acyclic stereotriads with potential usefulness as synthetic intermediates.
Novel isomerically pure tetrasubstituted allylboronates: Stereocontrolled synthesis of α-exomethylene γ-lactones as aldol-like adducts with a stereogenic quaternary carbon center
Kennedy, Jason W. J.,Hall, Dennis G.
, p. 898 - 899 (2007/10/03)
In spite of their inherent isomerization tendency and low reactivity, 1-alkoxycarbonyl vinylcopper(I) intermediates from the conjugate addition of organocuprates onto acetylenic esters were trapped with very high cis-addition selectivity with iodomethylboronic esters in the presence of HMPA. The resulting isomerically pure 3,3-disubstituted allylboronates react with aldehydes in a highly diastereo- and enantioselective manner, providing α-exomethylene γ-lactones with a stereogenic quaternary β-carbon center. Copyright
Unique regio- and stereoselectivity in the allylation of benzaldehyde with 2-substituted allylzincs generated by umpolung of π-allylpalladium
Shimizu, Masamichi,Kimura, Masanari,Tanaka, Shuji,Tamaru, Yoshinao
, p. 609 - 612 (2007/10/03)
α,β-Disubstituted allylzincs with alkoxycarbonyl as the β-substituent, generated via an umpolung of in situ generated π-allylpalladium by transmetallation with diethylzinc, react with benzaldehyde at the most substituted allylic terminus to provide syn-γ-
