115352-38-0

Upstream product

• 2930-05-4 Benzyloxymethyl-oxiran 
• 1066-54-2 trimethylsilylacetylene 
• 6224-91-5 trimethyl(prop-1-ynyl)silane 
• 60656-87-3 benzyloxyacetoaldehyde 
• 129217-85-2 trimethyl (3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-1-yn-1-yl)silane 
• 100-39-0 benzyl bromide 
• 14593-43-2 benzyl allyl ether 

Downstream Products

• 115352-39-1 (+/-)-1-benzyloxy-4-pentyn-2-ol 
• 115352-40-4 [2-(1-Ethoxy-ethoxy)-pent-4-ynyloxymethyl]-benzene 
• 115352-48-2 (2S,6S)-2-Benzyloxymethyl-4-methyl-1,7-dioxa-spiro[5.5]undec-4-ene 
• 115352-41-5 (Z)-10-Benzyloxy-9-(1-ethoxy-ethoxy)-1-hydroxy-7-methyl-dec-6-en-5-one 

Relevant academic research and scientific papers

Zinc-catalyzed allenylations of aldehydes and ketones

The general zinc-catalyzed allenylation of aldehydes and ketones with an allenyl boronate is presented. Preliminary mechanistic studies support a kinetically controlled process wherein, after a site-selective B/Zn exchange to generate a propargyl zinc int

Alkyne hydrosilylation catalyzed by a cationic ruthenium complex: Efficient and general trans addition

The complex [Cp*Ru(MeCN)3]PF6 is shown to catalyze the hydrosilylation of a wide range of alkynes, Terminal alkynes afford access to α-vinylsilane products with good regioselectivity. Deuterium labeling studies indicate a clean trans

Ruthenium-catalyzed vinylsilane synthesis and cross-coupling as a selective approach to alkenes: benzyldimethylsilyl as a robust vinylmetal functionality.

[reaction: see text] Ruthenium-catalyzed alkyne hydrosilylation or silyl-alkyne Alder ene reactions provide entry into benzyldimethylsilyl (BDMS)-substituted alkenes. The BDMS-vinylsilanes are further elaborated through mild palladium-catalyzed cross coup

Remarkable catalytic activity of Me3Ga in the alkylation of hetero- substituted epoxides with alkynyllithiums

Regio- and stereoselective ring-opening reaction of hetero-substituted epoxides with alkynyllithiums can be catalyzed by Me3Ga with remarkable efficiency at 0-20°C via pentacoordinate chelate-type complex.

Pentacoordinate organoaluminum chemistry: Catalytic efficiency of Me3Al in the epoxide cleavage with alkynyllithiums

A new and highly effective catalytic method for epoxide alkynylations has been developed that involves the chelation-controlled alkylation of heterosubstituted epoxides with Me3Al via pentacoordinate organoaluminum complexes by taking advantage of the exceedingly high affinity of aluminum to oxygen. For example, reaction of epoxy ether, (1-benzyloxy)-3-butene oxide (1), in toluene with PhC?CLi under the influence of catalytic Me3Al (10 mol%) proceeded smoothly at 0 °C for 5 h to furnish the alkynylation product, 1-(benzyloxy)-6-phenylhex-5-yn-3-ol, in 76% yield [cf. 3% without Me3Al catalyst; 78% with stoichiometric Me3Al under similar conditions]. This represents the first catalytic procedure for the amphiphilic alkylation of epoxides. The participation of pentacoordinate Me3Al complexes of epoxy ethers of type 1 is emphasized by comparing the reactivity with the corresponding simple epoxide, 5-phenyl-1-pentene oxide, which was not susceptible to nucleophile attack of PhC?CLi with catalytic Me3Al under similar conditions. The pentacoordinate complex formation of Me3Al with epoxy ether 1 is characterized by low-temperature 13C and 27Al NMR spectroscopy. This approach is also applicable to the selective alkynylation of tosyl aziridines with adjacent ether functionality, which provides a promising method for amino alcohol synthesis.

Synthesis of a marine polyether toxin, okadaic acid [1]1 1 Full Paper corresponding to the communications, M. Isobe, Y. Ichikawa and T. Goto, Tetrahedron Lett., 26, 5199 (1985); M. Isobe, Y. Ichikawa, D-L. Bai and T. Goto, Tetrahedron Lett., 26, 5203 (1985). - strategy and synthesis of segment a

The title compound was divided into three retrosynthetic segments A, B and C, by disconnecting two C-C bonds at C- 14 15 and C- 27 28. Segment A for okadaic acid synthesis comprises the carbon skeleton from C-1 through C-14, which was further disconnected at the bonds between C-8 and C-9 into two fragments A1 and A2. Each fragment was synthesized in the optically active form from D-glucose derivatives. Key steps are the oxymercuration and anti-selective heteroconjugate addition to elaborate the asymmetric carbons on acyclic parts of these fragments. The coupling was facilitated between the acetylenic carbanion and the lactone carbonyl of the respective fragments. The segment A was synthesized in 36 steps.