153668-22-5

Upstream product

• 17510-47-3 3-trimethylsilyloxy-2-pentene 
• 100-52-7 benzaldehyde 
• 96-22-0 pentan-3-one 
• 51425-54-8 (Z)-3-trimethylsiloxy-2-pentene 
• 51425-53-7 (E)-3-[(trimethylsilyl)oxy]pent-2-ene 
• 1072-72-6 Tetrahydrothiopyran-4-one 
• 784143-65-3 (3S,1'R)-3-[(1'-hydroxy-1'-phenyl)methyl]-tetrahydrothiopyran-4-one 
• 570385-67-0 (E)-trichloro-[(1-ethylpropenyl)oxy]-silane 

Relevant academic research and scientific papers

Chiral Br?nsted Acid as a True Catalyst: Asymmetric Mukaiyama Aldol and Hosomi-Sakurai Allylation Reactions

Highly diastereo- and enantioselective Mukaiyama aldol reaction catalyzed by a new chiral Br?nsted acid, N-(perfluorooctanesulfonyl)thiophosphoramide, is described. The perfluorooctyl substituent on the sulfonyl group of the catalyst plays an essential role in the stereoselection. The catalyst also allows the asymmetric Hosomi-Sakurai allylation, which has been considerably challenging due to the low reactivity of allylsilanes. 29Si and 31P NMR monitoring reveals the characteristic feature of the thiophosphoramide catalyst, acting as a strong Br?nsted acid even in the presence of excess silyl nucleophiles, which cannot be found in other related phosphoric acid analogues.

Investigation of a novel diamine based chiral auxiliary in the asymmetric alkylation of ketones

A novel chiral auxiliary containing a pyrrolidine ring has been utilised in the preparation of various chiral ketones with good to excellent enantioselectivities (up to 92%). It has been successfully employed in aldol and Michael reactions giving moderate to high selectivity.

A new class of ligands for aqueous, lanthanide-catalyzed, enantioselective Mukaiyama aldol reactions

The development of aqueous methods for generating enantiopure β-hydroxy carbonyl compounds is an important goal because these subunits compose many bioactive compounds and the ability to synthesize these groups in water has environmental and cost benefits. In this communication, we report a new class of ligands for aqueous, lanthanide-catalyzed, asymmetric Mukaiyama aldol reactions for the synthesis of chiral β-hydroxy ketones. Furthermore, we have used luminescence-decay measurements to unveil mechanistic information regarding the catalytic reaction via changes in water-coordination number. The precatalysts presented here yielded β-hydroxy carbonyls from aliphatic and aryl substrates with outstanding syn:anti ratios and enantiometric excesses of up to 49:1 and 97%, respectively.

Enantioselective aldol reactions of trichlorosilyl enol ethers catalyzed by the chiral phosphine oxide BINAPO

The enantioselective aldol reactions of aldehydes with trichlorosilyl enol ethers catalyzed by chiral phosphine oxide BINAPO afforded the corresponding aldol adducts with high diastereo- and enantioselectivities. Georg Thieme Verlag Stuttgart.

Aqueous asymmetric Mukaiyama aldol reaction catalyzed by chiral gallium Lewis acid with trost-type semi-crown ligands

The combination of Ga(OTf)3 with chiral semi-crown ligands (1a-e) generates highly effective chiral gallium Lewis acid catalysts for aqueous asymmetric aldol reactions of aromatic silyl enol ethers with aldehydes. A ligand-acceleration effect was observed. Water is essential for obtaining high diastereoselectivity and enantioselectivity. The p-phenyl substituent in aromatic silyl enol. ether (2 h) plays an important role and increases the enantioselectivity up to 95% ee. Although aliphatic silyl enol ethers provided low enantioselectivities and silylketene acetal is easily hydrolyzed in aqueous alcohol, the aldol reactions of silylketene thioacetal (12) with aldehydes in the presence of gallium-Lewis acid catalysts give the β-hydroxy thioester with reasonable yields and high diastereo- (up to 99:1) and enantioselectivities (up to 96% ee).

A highly enantioselective, moderately anti-selective aldol reaction using a novel hydrazone moiety as stereo director

The use of novel hydrazones as stereo directors with a view to develop a highly enantioselective, anti-diastereoselective aldol addition procedure has been investigated. A number of proline-derived hydrazones were produced and their effectiveness in direc

Proline-catalyzed asymmetric aldol reactions of tetrahydro-4H-thiopyran-4- one with aldehydes

Proline-catalyzed enantioselective direct intermolecular aldol reactions of tetrahydro-4H-thiopyran-4-one with various aldehydes give anti adducts with high diastereo- and enantioselectivities in moderate to excellent yields. With the aromatic aldehydes b

Stereoselective aldol additions of achiral ethyl ketone-derived trichlorosilyl enolates

Methods for the preparation of geometrically defined enoxy(trichlorosilanes) derived from ethyl ketone enolates have been developed. The addition of enoxy(trichlorosilanes) (trichlorosilyl enolates) to aldehydes proceeds with good yields in the presence of catalytic amounts of chiral phosphoramides. The reaction of Z-trichlorosilyl enolates to aryl aldehydes affords aldol products with good to excellent diastereo- and enantioselectivities. Phosphoramide-catalyzed aldol additions lacked substrate generality providing modest selectivities with unsaturated and aliphatic aldehydes. In all cases, the phosphoramide-catalyzed aldol addition of E-trichlorosilyl enolates to aldehydes provided good yields with moderate to good stereoselectivities.

Insight into the mechanism of direct catalytic aldol addition mediated by ambifunctional titanium complexes

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.