- Direct carbon-carbon bond formation via reductive soft enolization: A kinetically controlled syn-aldol addition of α-halo thioesters and enolizable aldehydes
-
The direct addition of enolizable aldehydes and α-halo thioesters to produce β-hydroxy thioesters enabled by reductive soft enolization is reported. The transformation is operationally simple and efficient and has the unusual feature of giving high syn-se
- Sauer, Scott J.,Garnsey, Michelle R.,Coltart, Don M.
-
supporting information; experimental part
p. 13997 - 13999
(2010/12/24)
-
- Ti-direct, powerful, stereoselective aldol-type additions of esters and thioesters to carbonyl compounds: Application to the synthesis and evaluation of lactone analogs of jasmone perfumes
-
An efficient TiCl4-Et3N or Bu3N-promoted aldol-type addition of phenyl and thiophenyl esters or thioaryl esters with aldehydes and ketones was performed (total 46 examples). The present method is advantageous from atom-economical and cost-effective viewpoints; good to excellent yields, moderate to good syn-selectivity, substrate variations, reagent availability, and simple procedures. Utilizing the present reaction as the key step, an efficient short synthesis of three lactone [2(5H)-furanone] analogs of jasmine perfumes was performed. Among them, the lactone analog of cis-jasmone had a unique perfume property (tabac). The Royal Society of Chemistry.
- Nagase, Ryohei,Matsumoto, Noriaki,Hosomi, Kohei,Higashi, Takahiro,Funakoshi, Syunsuke,Misaki, Tomonori,Tanabe, Yoo
-
p. 151 - 159
(2008/03/28)
-
- A facile and efficient direct aldol addition of simple thioesters
-
Simple thioesters undergo direct aldol addition to aldehydes in the presence of MgBr2·OEt2 and i-Pr2NEt using untreated, reagent-grade CH2Cl2 under atmospheric conditions. The reactions proceed extrem
- Yost, Julianne M.,Zhou, Guoqiang,Coltart, Don M.
-
p. 1503 - 1506
(2007/10/03)
-
- Phosphine/Lewis acid mediated Reformatsky-type reaction of α-bromoketone or -thioester derivatives
-
The combination of (?-tolyl)3P/TiCl4 effectively promoted the Reformatsky-type reaction of α-bromoketone or -thioester derivatives with various aldehydes, and the corresponding β-hydroxy carbonyl compounds were obtained in good yield
- Hashimoto, Yukihiko,Kikuchi, Satoshi
-
p. 126 - 127
(2007/10/03)
-
- Powerful stereoselective aldol-type additions of phenyl and phenylthio esters with aldehydes or ketones mediated by TiCl4/amine reagent
-
An efficient TiCl4/amine-promoted aldol-type addition of phenyl and phenylthio esters with aldehydes or ketones has been performed. The present method includes a practical merit from the green chemical viewpoint with regard to yields, variations of substrates, availability of reagents, and simple operations.
- Tanabe,Matsumoto,Funakoshi,Manta
-
p. 1959 - 1961
(2007/10/03)
-
- Diastereoselective Aldol Condensation of Silyl Ketene Acetal of 2-Pyridyl Thioester with Benzaldehyde
-
The TiCl4-mediated aldol reaction of the (E)-O-silyl ketene-O,S-acetal derived from 2-pyridyl thioester with benzaldehyde gave exclusively syn-aldol product.In contrast, BF3-mediated reaction afforded the corresponding anti-isomer as a major product.Chela
- Suh, Kwee-Hyun,Choo, Dong-Joon
-
p. 6109 - 6112
(2007/10/02)
-
- Diastereoselective aldol condensation of directly generated titanium enolates of activated esters
-
Simply generated (TiCl4, Et3N, -78°C) titanium enolates of some thioesters and α-thio substituted esters undergo aldol condensations with achiral and chiral aldehydes with low to high stereoselectivity. An 1H-NMR study of
- Annunziata, Rita,Cinquini, Mauro,Cozzi, Franco,Cozzi, Pier Giorgio,Consolandi, Emanuela
-
p. 7897 - 7910
(2007/10/02)
-
- STEREOSELECTIVE ALDOL CONDENSATIONS VIA ENOLBORONATES
-
Enolboronates, new enolates directly accessible from carbonyl compounds, exhibit extraordinary high erythro diastereoselection both with aliphatic and aromatic aldehydes.
- Gennari, Cesare,Cardani, Silvia,Colombo, Lino,Scolastico, Carlo
-
p. 2283 - 2286
(2007/10/02)
-