164203-14-9

Upstream product

• 109120-49-2 (S)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-(dimethyl-phenyl-silanyl)-3-phenyl-propan-1-one 
• 67263-06-3 3-(dimethyl(phenyl)silyl)-3-phenylpropanal 
• 94286-44-9 3-dimethyl(phenyl)silyl-3-phenylpropan-1-ol 
• 148003-99-0 benzyl (3RS)-3-dimethyl(phenyl)silyl-3-phenylpropanoate 
• 3839-31-4 dimethyl(phenyl)silyllithium 
• 591-51-5 phenyllithium 
• 109053-73-8 (3aS,6R,7aR)-8,8-dimethyl-1-[(2E)-3-phenylprop-2-enoyl]hexahydro-3a,6-methano-2,1-benzisothiazole 2,2-dioxide 
• 768-33-2 phenyldimethylsilyl chloride 
• 109053-88-5 (E)-3-[dimethyl(phenyl)silyl]propenoic acid 
• 109053-72-7 (E)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-(dimethyl-phenyl-silanyl)-propenone 

Downstream Products

• 109120-50-5 (2S,3S)-3-(Dimethyl-phenyl-silanyl)-2-methyl-3-phenyl-propionic acid methyl ester 
• 36041-80-2 (2R,3S)-methyl 3-hydroxy-2-methyl-3-phenylpropanoate 
• 36615-45-9 methyl (S)-3-hydroxy-3-phenylpropionate 

Relevant academic research and scientific papers

Diastereoselectivity in the Preparation of β-Silyl Esters from αβ-Unsaturated Esters and Amides Attachhed to Chiral Auxiliaries

The conjugate addition of the phenyldimethylsilyl-cuprate reagent to cinnamate and crotonate esters and amides 1 of various known chiral auxiliaries, a-e, is diastereoselective.The sense of diastereoselectivity of silyl-cuprate addition to the esters 1b-d, 8 and 9 is different from established precedent based on carbon-cuprates, but is normal for silyl-cuprate addition to the amide 1a, the imines 1e and 21, and the oxazolidine 6.The chiral auxiliary e gives the best results of those tested, and the silicon-containing group can be removed from the chiral auxiliary using alkoxide ion in aprotic media, making available β-silyl esters 27-29 of high enantiomeric excess, with recovery of the chiral auxiliary 30.

Dispiroketals in synthesis (Part 16): Functionalised dispiroketals as new chiral auxiliaries; the synthesis of dihydroxylated dispiroketals in optically pure form and their application as bifunctional , C2-symmetrical, chiral auxiliaries for highly stereoselective Michael additions

A range of rigid, architecturally complex diols derived from dispiroketals have been synthesised.A bifunctional, C2-symmetrical, chiral auxiliary derived from these dihydroxylated dispiroketals has been used to induce a high degree of asymmetry in Michael additions of cuprates to a variety of di-α,β-unsaturated ester systems.

Preparation of Enantiomerically Pure β-Silylcarboxyl Derivatives by Asymmetric 1,4-Addition to N-Enoyl-sultams

EtAlCl2-promoted additions of organocopper reagents to camphor-derived, conjugated N-enoyl-sultams gave saturated and olefinic β-silylcarboxyl derivatives with high diastereodifferentiation.Nondestructive removal of the chiral auxiliary followed by oxidative Si-C bond cleavage furnished enantiomerically pure acetate-derived aldols and propionate-derived 'anti'-aldols (via silyl-directed α-methylation).