70975-25-6

Upstream product

• 13829-77-1 3-(trimethylsilyl)-1-phenyl-2-propyn-1-one 
• 89530-34-7 1-phenyl-3-trimethylsilylprop-2-yn-1-ol 
• 54655-07-1 lithium trimethylsilylacetylenide 
• 100-52-7 benzaldehyde 
• 1066-54-2 trimethylsilylacetylene 
• 401614-03-7 1-phenylseleno-1-[(S)-p-tolylsulfinyl]-2-(trimethylsilyl)ethane 
• 153123-03-6 (E)-1-[(R)-p-tolylsulfinyl]-2-(trimethylsilyl)ethylene 
• 153123-09-2 (R_S)-p-Tolyl β-(trimethylsilyl)ethyl sulfoxide 
• 153123-05-8 (S_S,S)-(E)-1-phenyl-2-(p-tolylsulfinyl)-3-(trimethylsilyl)-2-propen-1-ol 

Downstream Products

• 4187-87-5 (R)-1-phenyl-2-propyn-1-ol 
• 84681-19-6 (R)-(+)-1-phenyl-prop-2-yn-1-acetyloxy 

Relevant academic research and scientific papers

A Straightforward Sequential Approach for the Enantioselective Synthesis of Optically Active α-Arylmethanol-1,2,3-Triazoles

Herein we describe a compelling sequential methodology for obtaining optically active α-arylmethanols-1,2,3-triazoles. The approach is based on the enantioselective alkynylation of aldehydes followed by a one-pot two-step desilylation/CuI-catalyzed azide-alkyne 1,3-dipolar cycloaddition (CuAAC), providing the corresponding products with excellent yields and high levels of enantioselectivity. Furthermore, the click chemistry can be performed without affecting the enantiomeric excess. The application of the reaction has been demonstrated in the synthesis of a 1,2,3-triazole analog of antihistaminic and anticholinergic drug (R)-orphenadrine.

Lithium binaphtholate-catalyzed asymmetric addition of lithium acetylides to carbonyl compounds

The asymmetric addition of lithium acetylides to carbonyl compounds in the presence of a chiral lithium binaphtholate catalyst was developed. A procedure involving the slow addition of carbonyl compounds to lithium acetylides improved the enantioselectivi

Highly enantioselective addition of trimethylsilylacetylene to aldehydes catalyzed by a zinc-amino-alcohol complex

A fine addition! A highly enantioselective and efficient procedure for the amino-alcohol-zinc-catalyzed addition of trimethylsilylacetylene to aromatic, α,β-unsaturated, and aliphatic aldehydes has been developed (see scheme; R=aryl, alkynyl, or alkyl; TMS=trimethylsilyl; TBDMS=tert- butyldimethylsilyl). The present protocol was successfully applied in the concise synthesis of the natural products marine alkynol and falcarindiol. Copyright

Gold-catalyzed regioselective hydration of propargyl acetates assisted by a neighboring carbonyl group: Access to α-acyloxy methyl ketones and synthesis of (±)-actinopolymorphol B

A general atom-economical approach for the synthesis of α-acyloxy methyl ketone is demonstrated through regioselective hydration of a wide range of propargyl acetates. Readily available catalyst comprising of 1% Ph 3PAuCl and 1% AgSbF6 in dioxane-H2O efficiently hydrolyzes the terminal alkynes of the propargyl acetate in the absence of acid promoters at ambient temperature within a short time. Effective regioselective hydration is facilitated by the neighboring carbonyl group as demonstrated through 18O-labeling study. Compatibility of functional moieties and tolerance to various acid-labile protecting groups are observed. The catalytic condition is also suitable to perform hydration of TMS-substituted propargyl acetates, even though it requires prolonged reaction time for completion. Stereointegrity of the propargylic acetate is preserved during the hydration. The robustness of the system is successfully demonstrated through gram scale preparation of the product in nearly quantitative yield. The common α-acyloxy methyl ketone is transformed to 1,2-diol and 1,2-amino alcohol derivatives. Synthesis of actinopolymorphol B is achieved for the first time involving hydration of the propargyl acetate as the key step.

3,3′-anisyl-substituted BINOL, H4BINOL, and H 8BINOL ligands: Asymmetric synthesis of diverse propargylic alcohols and their ring-closing metathesis to chiral cycloalkenes

(Chemical Equation Presented) A series of optically active BINOL, H 4BINOL, and H8BINOL derivatives were prepared. These compounds in combination with ZnEt2 and Ti(OiPr) 4 were used to catalyze the asymmetric reaction of alkynes with aldehydes to generate chiral propargylic alcohols at room temperature. Through this comparative study, a 3,3′-bisanisyl-substituted H8BINOL (S)-7 was found to be a generally enantioselective catalyst for the reaction of structurally diverse terminal alkynes with a variety of aldehydes. It catalyzed the reactions of alkyl propiolates with 88-99% ee; the reactions of phenylacetylene with 81-87% ee; the reactions of 4-phenyl-1-butyne, an alkyl alkyne, with 77-89% ee; and the reactions of trimethylsilylacetylene with 92-97% ee. The optically active propargylic alcohols generated from this catalytic asymmetric alkyne addition were observed to undergo efficient ring-closing-metathesis (RCM) reaction in the presence of the Grubbs II catalyst to produce chiral cycloalkenes. It was further found that some of the chiral propargylic alcohols underwent a highly chemoselective tandem RCM hydrogenation reaction with retention of the enantiomeric purity. 2009 American Chemical Society.

l-Proline-derived tertiary amino alcohol as a new chiral ligand for enantioselective alkynylation of aldehydes

The easily prepared chiral tertiary amino alcohol 1a was found to catalyze the reaction of alkynylzinc reagents with various aldehydes to generate chiral propargylic alcohols with moderate-to-good enantioselectivities. The mechanism of the reaction is als

Amino thiols versus amino alcohols in the asymmetric alkynylzinc addition to aldehydes

A series of modular amino thiol and amino alcohol ligands have been synthesized in enantiopure form from common enantiopure precursors. Their structures have been optimized for performance in the asymmetric alkynylzinc addition to aldehydes, and a direct

Catalytic enantioselective addition of terminal alkynes to aromatic aldehydes using zinc-hydroxyamide complexes

A mandelamide ligand, derived from (S)-mandelic acid and (S)-phenylethanamine, catalyzes the addition of aryl-, alkyl- and silyl-alkynylzinc reagents to aromatic and heteroaromatic aldehydes with good yields and good to high enantioselectivities.

Facile, mild, and highly enantioselective alkynylzinc addition to aromatic aldehydes by BINOL/N-methylimidazole dual catalysis

(Chemical Equation Presented) The dual Lewis acid/base catalytic system, generated from N-methylimidazole (NMI), (R)-1,1′-bi-2-naphthol [(R)-BINOL], and Ti(OiPr)4, effectively catalyzes the enantioselective alkynylation of aldehydes in the pres

Enantioselective alkynylation of aldehydes catalyzed by [2.2]paracyclophane-based ligands

[2.2]Paracyclophane-based ketimine ligands were evaluated as catalysts for the enantioselective addition of in situ-prepared alkynylzinc reagents to aldehydes. The initial high activity and enantioselectivity of these ligands could be improved by an addit