51105-91-0

Upstream product

• 76-86-8 Triphenylsilyl chloride 
• 107-19-7 propargyl alcohol 
• 50-00-0 formaldehyd 
• 6229-00-1 triphenylsilylacetylene 

Downstream Products

• 104755-56-8 (E)-3-(Triphenylsilyl)<2,3-(2)H2>prop-2-en-1-ol 
• 151710-76-8 (Z)-3-Iodo-3-triphenylsilanyl-prop-2-en-1-ol 
• 101844-27-3 (E)-3-(triphenylsilyl)-2-propen-1-ol 
• 69618-26-4 3-(triphenylsilyl)propiolaldehyde 
• 263720-62-3 (3-Bromo-prop-1-ynyl)-triphenyl-silane 
• 850172-10-0 buta-2,3-dien-2-yltriphenylsilane 

Relevant academic research and scientific papers

Ni-catalyzed direct carboxylation of propargylic alcohols with carbon dioxide

The carboxylation of propargylic alcohols containing a silyl group at the terminal position was conducted in a CO2 atmosphere at atmospheric pressure in the presence of a nickel catalyst and diethylzinc. Here, CO2 was used as not only the C1 source but also the promoter of the COH cleavage processes for the oxidative addition of propargylic alcohols.

Access to Stereodefined (E)-2-Silylallylboronates via Regioselective Chloroboration of Allenylsilanes

A catalyst-free method for the highly regioselective chloroboration of allenylsilanes is described. In the presence of BCl3 and 2,6-lutidine, chloroboration of allenylsilanes proceeds smoothly without any catalyst, and the product could be treated with pinacol to afford the corresponding pinacol borates in one-pot reaction. This reaction provides a direct approach to construct valuable 2-silylallylboronate frameworks with operational simplicity and high atom-economy.

Synthesis of Cryptochiral (R,R)-2,3-Dideuterooxirane as Stereochemical Reference Compound and Chemical Correlation with D-(+)-Glyceraldehyde

Chirality plays a pivotal role in chemistry and biology, e.g., structure-specific targeting in drug development or the lock-and-key theory of enzyme interactions. Determining absolute configurations of chiral molecules is essential to understanding such mechanisms and to developing chemical processes involving chiral compounds. In particular, this becomes obvious in the understanding of chemical reaction networks in the context of the origins of life. A stereochemical reference compound that can be correlated with sugars, amino acids, etc. is of great interest. Here, we present the synthesis of enantiopure (R,R)-2,3-dideuterooxirane, of which the absolute configuration has been unambiguously determined by foil-induced Coulomb explosion imaging, and the correlation with the configuration of D-(+)-glyceraldehyde.

Synthesis and Isolation of Organogold Complexes through a Controlled 1,2-Silyl Migration

During our efforts toward the synthesis of naturally occurring polyprenylated polycyclic acylphloroglucinol using a AuI-catalyzed 6-endo dig carbocyclization, we isolated stable vinyllic gold intermediates. Optimization lead to isolated yields of up to 98 %, using 2-(di-tert-butylphosphino)biphenyl as the ligand. This transformation is derived from a silyl rearrangement that can be fully controlled according to the nature of the substituent on the ynone. This selective transformation does not require basic conditions to prevent protodeauration. These vinylgold complexes are the first isolated intermediates during a silyl migration with gold(I). More than 16 new organogold complexes were synthesized and characterized by single-crystal X-ray diffraction. Reactivity of these complexes is also presented.

Stereoselective synthesis of complex polycyclic aziridines: Use of the Bronsted acid-catalyzed aza-Darzens reaction to prepare an orthogonally protected mitomycin C intermediate with maximal convergency

A concise synthesis of a highly functionalized intermediate lacking only C10 of the mitomycin backbone is described. The key to this development is the Bronsted acid-catalyzed aza-Darzens reaction used to forge the cis-aziridine. Additionally an oxidative

A direct and stereocontrolled route to conjugated enediynes

A unified synthetic route to 3-hex-en-1,5-diynes, a key building block found in many of the enediyne antitumor agents and designed materials, was developed. The method, which relies on a carbenoid coupling-elimination strategy is tolerant of a wide range of functionalities, and was applied to the synthesis of a variety of linear and cyclic enediynes. Reaction parameters can be adjusted to control stereoselectivity of the process, producing linear enediynes from 1:12 to >100:1 E:Z ratio, and in the case of cyclic enediynes, giving the exclusively Z C-9, C-10, or C-11 products. Key features of the process are the ready availability of precursors and the mildness and efficiency of the reaction. Application of the process in the design of materials precursors and preparation of enediyne antitumor agents are presented.

Stereochemical control in the metallohalocarbenoid route to linear enediynes

Methods for the stereoselective preparation and unmasking of disubstituted Z enediynes are reported. The origins of the unprecedented stereoselectivity of the process are uncovered.

Optically active acylsilanes. Synthesis of selected 2,3-O-isopropylidene-1-(trialkyl/arylsilyl)glyceraldehyde derivatives

Syntheses of 1-trimethylsilyl-, 1-tert-butyldimethylsilyl, 1-dimethylphenylsilyl- and 1-triphenylsilyl-2,3-O-isopropylideneglyceraldehyde derivatives, 6a, 6b, 6c, and 6d, respectively, is described.

Synthesis of (2R,3R)- and (2S,3S)-Oxirane and Application of It to the Synthesis of Chirally Labeled Homoserine

(2R,3R)- and (2S,3S)-oxirane have been synthesized from 2-propynol, the key step being the asymmetric epoxidation of (E)-3-(triphenylsilyl)-2-propenol.To determine the enantiomeric purities of the oxiranes, they were reacted with phenyllithium,

Chirally-labelled Oxirane

(R,R)- and (S,S)-oxiranes have been synthesized from prop-2-yn-1-ol, the key step being asymmetric epoxidation of (E)-3-(triphenylsilyl)prop-2-en-1-ol.