141186-06-3

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 31593-39-2 2-phenethyl-[1,3]dithiane 
• 104-53-0 3-phenyl-propionaldehyde 

Downstream Products

• 61157-31-1 3-phenylpropionyltrimethylsilane 
• 104376-05-8 1-cyclopentylidene-4-phenyl-2-butanone 
• 73341-06-7 1-phenyl-3-((trimethylsilyl)oxy)3,4-octendiene 
• 104376-04-7 (1-Cyclopentylidenemethylene-3-phenyl-propoxy)-trimethyl-silane 
• 73341-04-5 5-methyl-1-phenyl-3-((trimethylsilyl)oxy)-3,4-nonadiene 
• 73341-07-8 2,6-diphenyl-4-trimethylsiloxy-2,3-hexadiene 
• 90729-70-7 (E)-1,5-diphenyl-4-hexen-3-one 
• 104376-01-4 1-phenyl-4-octen-3-one 
• 501-52-0 3-Phenylpropionic acid 

Relevant academic research and scientific papers

Intermolecular Schmidt reaction of alkyl azides with acyl silanes

The first intermolecular Schmidt reaction of alkyl azides with acyl silanes has been designed and realized, producing a range of amides with absolute site selectivity in good to excellent yields. The mechanism of the conversion has been proposed, and the reaction exhibits scope of substrates.

Brook/Elimination/Aldol Reaction (BEAR) Sequence for the Direct Preparation of Fluorinated Aldols from β,β-Difluoro-α-(trimethylsilyl)alcohols

A methodology allowing the preparation of aldols featuring a fluorinated stereogenic center is reported. The corresponding fluoroenolates are formed in situ from stable β,β-difluoro-α-(trimethylsilyl)alcohols, through a base-mediated process involving a Brook rearrangement followed by a fluoride elimination, and are directly added to aromatic aldehydes. Two different sets of conditions were disclosed. The first one involves the stoichiometric addition of potassium tert-butoxide (t-BuOK) while the second is based on the use of a catalytic amount of an ammonium phenoxide. The latter opens the way for a catalytic and asymmetric version of this Brook/elimination/aldol reaction (BEAR) sequence.

Chemoselective Amide-Forming Ligation Between Acylsilanes and Hydroxylamines Under Aqueous Conditions

We report the facile amide-forming ligation of acylsilanes with hydroxylamines (ASHA ligation) under aqueous conditions. The ligation is fast, chemoselective, mild, high-yielding and displays excellent functional-group tolerance. Late-stage modifications of an array of marketed drugs, peptides, natural products, and biologically active compounds showcase the robustness and functional-group tolerance of the reaction. The key to the success of the reaction could be the possible formation of the strong Si?O bond via a Brook-type rearrangement. Given its simplicity and efficiency, this ligation has the potential to unfold new applications in the areas of medicinal chemistry and chemical biology.

1,2-Amino Alcohols via Cr/Photoredox Dual-Catalyzed Addition of α-Amino Carbanion Equivalents to Carbonyls

Herein, we report the synthesis of protected 1,2-amino alcohols starting from carbonyl compounds and α-silyl amines. The reaction is enabled by a Cr/photoredox dual catalytic system that allows the in situ generation of α-amino carbanion equivalents which act as nucleophiles. The unique nature of this reaction was demonstrated through the aminoalkylation of ketones and an acyl silane, classes of electrophiles that were previously unreactive toward addition of alkyl-Cr reagents. Overall, this reaction broadens the scope of Cr-mediated carbonyl alkylations and discloses an underexplored retrosynthetic strategy for the synthesis of 1,2-amino alcohols.

Stereoselective syntheses of trisubstituted olefins via platinum catalysis: α-Silylenones with geometrical complementarity

The stereoselective syntheses of α-silylenones using catalytic PtCl2 are reported. Via alkyne activation, α- hydroxypropargylsilanes are converted to (Z)-silylenones through a highly selective silicon migration. The complementary (E)-silylenone