318967-94-1Relevant academic research and scientific papers
Stereoselective Halo-Succinimide Facilitated α-Halogenations of Substituted α-Trialkylsilyl-β-Substituted-α,β-Unsaturated Esters
Jennings, Michael P.,Probasco, Kristina C.
, p. 8945 - 8954 (2021/07/20)
The NXS (X = Cl, Br)-mediated halogenation of a series of (E)-α-trimethylsilyl-β-alkyl(aryl)-α,β-unsaturated esters in dimethylformamide (DMF) has furnished (Z)-β-substituted-α-halogenated-α,β-unsaturated ester products in moderate to high isolated yields (58-90%) with dr values of >20:1 coupled with the inversion of olefin stereochemistry. The reaction process was hypothesized to include an initial halonium cation intermediate, followed by regioselective ring opening with DMF. Subsequentanti-E2-type concomitant elimination allowed for the stereoselective formation of the product vinylic bromo-and chloroesters.
Stereoselective preparation of (E)-α-bromoacrylates from mixtures of brominated ando phosphonates
Olpp, Thomas,Brueckner, Reinhard
, p. 2135 - 2152 (2007/10/03)
We prepared 69:31-11:89 mixtures of phosphonates 6b and 7b containing two phenoxy substituents, a CO2Et group, and 1 or 2 bromine atoms, respectively, at the interspersed methylene group. Deprotonating 64:36 mixtures of these reagents with NaH
SUBSTITUTED ARYLCYCLOPROPYLACETAMIDES AS GLUCOKINASE ACTIVATORS
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Page 31; 106-107, (2008/06/13)
According to the present invention there is provided a compounds of formula (I): and pharmaceutically acceptable salts thereof.
A highly stereoselective synthesis of (E)-α-bromoacrylates
Tago, Keiko,Kogen, Hiroshi
, p. 8825 - 8831 (2007/10/03)
Novel reagent, methyl bis(2,2,2-trifluoroethoxy)bromophosphonoacetate (5a), was designed and prepared in order to efficiently synthesize (E)-α-bromoacrylates 7, from which widely useful precursors for various C-C bond formations were prepared. Horner-Wadsworth-Emmons (HWE) reaction of various aldehydes with 5a in the presence of t-BuOK and 18-C-6 gave corresponding (E)-α-bromoacrylate derivatives with high stereoselectivity and excellent yield. Using the product (E)-α-bromoacrylate 7s as a key intermediate, we succeeded in developing the most effective route of plaunotol synthesis via Suzuki cross-coupling. (C) 2000 Elsevier Science Ltd.
