102285-76-7Relevant articles and documents
ZIRCONIUM ENOLATES AS A NEW ERYTHRO-SELECTIVE ALDOL CONDENSATION REAGENT
Yamamoto, Yoshinori,Maruyama, Kazuhiro
, p. 4607 - 4610 (1980)
Zirconium enolates, prepared from lithium enolates, ans bis(cyclopentadienyl)zirconium dichloride, undergo a facile aldol condensation with aldehydes to give predominantly the erythro product regardless of the geometry of the starting enolates.
Rh-catalyzed aldehyde - Aldehyde cross-aldol reaction under base-free conditions: In situ aldehyde-derived enolate formation through orthogonal activation
Lin, Luqing,Yamamoto, Kumiko,Matsunaga, Shigeki,Kanai, Motomu
, p. 2974 - 2983 (2013)
The chemoselective generation of aldehyde-derived enolates to realize an aldehyde - aldehyde cross-aldol reaction is described. A combined Rh/dippf system efficiently promoted the isomerization/aldol sequence by using primary allylic, homoallylic, and bishomoallylic alcohols; secondary allylic and homoallylic alcohols; and trialkoxyboranes that were derived from primary allylic and homoallylic alcohols. The reaction proceeded at ambient temperature under base-free conditions, thus giving cross-aldol products with high chemoselectivity. Mechanistic studies, as well as its application to double-aldol processes under protecting-group-free conditions, are also described. Copyright
Major Effect of the Leaving Group in Dialkylboron Chlorides and Triflates in Controlling the Stereospecific Conversion of Ketones into either (E)- or (Z)-Enol Borinates
Brown, Herbert C.,Dhar, Raj K.,Bakshi, Raman K.,Pandiarajan, Paul K.,Singaram, Bakthan
, p. 3441 - 3442 (1989)
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STEREOSELECTIVE ALDOL CONDENSATIONS VIA ALKENYLOXY DIALKYOXYBORANES: MECHANISTIC AND STEREOCHEMICAL DETAILS.
Gennari, Cesare,Colombo, Lino,Scolastico, Carlo,Todeschini, Roberto
, p. 4051 - 4058 (1984)
A detailed investigation of the enolization of ketones with ethylenechloroboronate (ECB) in the presence of a tertiary amine and the subsequent aldol condensations of these boron enolates was conducted.The enolization with ECB-DPEA system was found to be
erythro-Selective Aldol Condensation via Triphenyltin Enolates. Stereoselection Independent of the Stereochemistry of the Enolates
Yamamoto, Yoshinori,Yatagai, Hidetaka,Maruyama, Kazuhiro
, p. 162 - 163 (1981)
Triphenyltin enolates, prepared from lithium enolates and triphenyltin chloride, undergo a rapid aldol condensation with aldehydes without the need for the presence of Lewis acids to give predominantly the erythro-product regardless of the geometry of the starting enolates.
Novel Reactive Silyl Enolates. Highly Stereoselective Aldol and Michael Reactions without Catalysts
Kobayashi, Shu,Nishio, Koichi
, p. 2647 - 2649 (1993)
Novel silyl enolates, prepared in situ from ketones and dimethylsilyl ditriflate (Me2Si(OTf)2) in the presence of a tertiary amine, reacted smoothly with electrophiles such as aldehydes, acetals, or α,β-unsaturated ketones without catalyst at -78 deg C to
Gallium(III) triflate catalyzed diastereoselective mukaiyama aldol reaction by using low catalyst loadings
Plancq, Baptiste,Justafort, Lyse Carole,Lafantaisie, Mathieu,Ollevier, Thierry
, p. 6525 - 6529 (2013)
A mild method for the diastereoselective Mukaiyama aldol reaction is reported. By using a low loading of the gallium(III) triflate catalyst (down to 0.01 mol-%), the transformation proceeds efficiently to afford the corresponding β-hydroxy ketones in yields up to 92a€‰%. To the best of our knowledge, this is the first report of a metal triflate acting as a safe, bench-stable, and slow-releasing source of triflic acid for the Mukaiyama aldol reaction. A diastereoselective Mukaiyama aldol reaction was performed under mild conditions with a low loading of the gallium(III) triflate catalyst (down to 0.01 mol-%). The transformation proceeded efficiently to afford the corresponding β-hydroxy ketones in yields up to 92a€‰%. Copyright
Unusual highly regioselective direct aldol additions with a moisture-resistant and highly efficient titanium catalyst
Mahrwald, Rainer,Schetter, Bernd
, p. 281 - 284 (2006)
The extremely robust and water-stable tetranuclear complex Ti 4(μ-BINOLato)6(μ3-OH)4 was found to catalyze the direct aldol addition with high regioselectivities at the more steric α-encumbered side of unsymmetr
Insight into the mechanism of direct catalytic aldol addition mediated by ambifunctional titanium complexes
Mahrwald,Ziemer
, p. 4459 - 4461 (2002)
X-Ray structure analysis of a titanium(IV) isopropoxide/mandelic acid complex provides an insight into the mechanism of this novel direct enantioselective aldol addition. The catalytic cycle mediated by the titanium(IV) alkoxide/mandelic acid complex is presented.
Iridium-catalyzed crossed aldol coupling and a new concept to form an Ir-Si species
Matsuda, Isamu,Hasegawa, Yuki,Makino, Tatsuya,Itoh, Kenji
, p. 1405 - 1408 (2000)
[Ir(COD)(PPh3)2]X (X=PF6, ClO4, and OTf) activated by H2 molecule catalyzes Mukaiyama-type aldol coupling between enoxysilanes and acetals or aldehydes. An Ir-Si species formed in the first stage of t
