202744-51-2Relevant academic research and scientific papers
Synthesis of anti-l,3-Diols through RuCl3/PPh3-Mediated Hydrogenation of β-Hydroxy Ketones: An alternative to organoboron reagents
Roche, Christophe,Labeeuw, Olivier,Haddad, Mansour,Ayad, Tahar,Genet, Jean-Pierre,Virginie, Ratovelomanana-Vidal,Phansavath, Phannarath
experimental part, p. 3977 - 3986 (2010/02/27)
Hydrogenation of enantioenriched β-hydroxy ketones promoted by the catalyst generated in situ from commercially available and inexpensive RuCl 3 and PPh3 under hydrogen pressure allowed the efficient preparation of a variety of anti1
Chiral phosphoramide-catalyzed aldol additions of ketone trichlorosilyl enolates. Mechanistic aspects
Denmark, Scott E.,Pham, Son M.,Stavenger, Robert A.,Su, Xiping,Wong, Ken-Tsung,Nishigaichi, Yutaka
, p. 3904 - 3922 (2007/10/03)
The mechanism of the catalytic, enantioselective addition of trichlorosilyl enolates to aldehydes has been investigated. Kinetic studies using ReactIR and rapid injection NMR (RINMR) spectroscopy have confirmed the simultaneous operation of dual mechanist
The chemistry of trichlorosilyl enolates. Aldol addition reactions of methyl ketones
Denmark,Stavenger
, p. 8837 - 8847 (2007/10/03)
Investigations on the aldol addition chemistry of trichlorosilyl enolates derived from methyl ketones are presented in full. These trichlorosilyl enolates are competent aldol reagents in the absence of additives, reacting with aldehydes at ambient temperature to provide high yields of aldol adducts. When either enol or aldehyde partner bears a stereogenic center, low diastereoselectivity is observed in this uncatalyzed aldol process. The aldol additions are dramatically accelerated by the addition of catalytic quantities of chiral phosphoramides, particularly one derived from N,N'-dimethylstilbene-1,2-diamine. In this catalyzed mode, good to high enantioselectivities are obtained with a variety of achiral trichlorosilyl enolates and aldehydes. When either partner bears a stereogenic center, high diastereoselectivities are obtained with one enantiomer of the catalyst (matched case), while the other enantiomer provides low diastereoselectivity (mismatched case). The reaction scope, optimization of conditions, and stereoselection events are also discussed.
Catalytic Asymmetric Aldol-Type Reactions Using a Chiral (Acyloxy)borane Complex
Ishihara, Kazuaki,Maruyama, Tohru,Mouri, Makoto,Gao, Qingzhi,Furuta,Kyoji,Yamamoto, Hisashi
, p. 3483 - 3491 (2007/10/02)
In the presence of 20 molpercent of a chiral (acyloxy)borane (CAB) complex prepared from BH3*THF and a chiral mono-O-acylated tartaric acid, achiral silyl enol ethers or ketene silyl acetals react with achiral aldehydes to afford the corresponding aldol-t
Enantioselective Mukaiyama-aldol and aldol-dihydropyrone annulation reactions catalyzed by a tryptophan-derived oxazaborolidine
Corey,Cywin, Charles L.,Roper, Thomas D.
, p. 6907 - 6910 (2007/10/02)
The (S)-tryptophan derived catalyst 1, has been used to effect enantioselective Mukaiyama-aldol and aldol-dihydropyrone annulation reactions of trimethylsilyloxy olefins and dienes.
