79015-64-8Relevant academic research and scientific papers
Zinc catalyzed and mediated propargylations with propargyl boronates
Fandrick, Daniel R.,Fandrick, Keith R.,Reeves, Jonathan T.,Tan, Zhulin,Johnson, Courtney S.,Lee, Heewon,Song, Jinhua J.,Yee, Nathan K.,Senanayake, Chris H.
supporting information; experimental part, p. 88 - 91 (2010/03/03)
Chemical Equation Presented The utility of allenyl and propargyl boronates for the propargylation of aldehydes and ketones mediated by zinc is presented. The reaction is catalytic in zinc with allenyl or propargyl borolanes. The propargylation with crystalline and air-stable propargyl diethanolamine boronates was also achieved. A catalytic cycle is proposed, and preliminary mechanistic studies are discussed.
Carbonyl propargylation and allenylation with 2-propynyl mesylates, tin(IV) iodide, and tetrabutylammonium iodide controlled by either a steric effect or coordination effect
Masuyama, Yoshiro,Yamazuki, Ryouichi,Ohtsuka, Masaru,Kurusu, Yasuhiko
, p. 1750 - 1752 (2008/02/03)
A combination of tin(IV) iodide and tetrabutylammonium iodide can be used for propargylation or allenylation of aldehydes with 2-propynyl mesylates in dichloromethane. 1-Methyl-2-propynyl mesylate or 2-butynyl mesylate results in propargylation or allenyl
Indium-Mediated Reaction of Trialkylsilyl Propargyl Bromide with Aldehydes: Highly Regioselective Synthesis of Allenic and Homopropargylic Alcohols
Lin, Man-Jing,Loh, Teck-Peng
, p. 13042 - 13043 (2007/10/03)
High regioselective preparation of either the allenic alcohols or homopropargylic alcohols using the indium-mediated reaction of trialkylsilyl propargyl bromides with various aldehydes has been accomplished. By just changing the silyl groups and the react
On pentaorganylstiborane. III. Regio- and diastereoselective additions of acetylenic and allenic organoantimony compounds to aldehydes
Zhang, Li-Jun,Mo, Xue-Sheng,Huang, Yao-Zeng
, p. 77 - 86 (2007/10/02)
The reaction of propargyl bromide (4a) with tributylstibine gave allenyltributylstibonium bromide (5), and its corresponding pentaorganylstiborane reacted with aldehyde to give homopropargylic alcohol (10a) exclusively in good yield.However, the reaction
Gallium-Mediated Highly Regioselective Reactions of Trimethylallylpropargyl Bromide and Trimethylsilylallyl Bromide with Carbonyl Compounds
Han, Ying,Huang, Yao-Zeng
, p. 9433 - 9434 (2007/10/02)
One-pot reactions of gallium powder, trimethylsilylpropargyl bromide, aldehydes or ketones in the presence of KI and LiCl show very high acetylenic selectivity and under the same conditions, trimethylsilylallyl bromide also exhibits very high selectivity
Regioselective reactions of trimethylsilylpropargylic and trimethylsilylallylic organoantimony compounds with aldehydes
Zhang, Li-Jun,Mo, Xue-Sheng,Huang, Ji-Ling,Huang, Yao-Zeng
, p. 1621 - 1624 (2007/10/02)
The reactions of trimethylsilylallylic organoantimony compound with aldehydes show very high selectivity favoring α-adducts; and the reactions of trimethylsilylpropargylic organoantimony compounds with aldehydes also exhibit very high acetylenic selectivity (α-adducts) in the presence of LiBr.
Reactions of Carbonyl Compounds with diisobutyltelluronium Bromide Mediated by Different Strong Bases: Highly Regioselective Synthesis of (Trimethylsilyl)propargyl Alcohol and Highly Stereoselective Synthesis of cis-(Trimethylsilyl)alkynyl Epoxides
Zhou, Zhang-Lin,Huang, Yao-Zeng,Shi, Li-Lan,Hu, Jiong
, p. 6598 - 6603 (2007/10/02)
diisobutyltelluronium bromide (1), after being treated with alkyl- or aryllithium reagent, undergoes a lithium-tellurium exchange reaction via an unstable transient tetraorganyltellurium intermediate, and the in situ generated lithium species react with carbonyl compounds to give (trimethylsilyl)propargyl alcohols 2 in high yields with high regioselectivity.However, when the telluronium salt 1 was treated with nonnucleophilic bases such as LDA or lithium 2,2,6,6-tetramethylpiperidide, the moderately stabilized silylated telluronium ylide formed.The silylated telluronium ylide reacted with carbonyl compounds to afford (trimethylsilyl)alkynyl epoxides 11 in good to excellent yields with high cis stereoselectivity.
Enantioselective Epoxidation of Conjugated Dienes and Enynes. Trans-Epoxides from cis-Olefins
Lee, Nam Ho,Jacobsen, Eric N.
, p. 6533 - 6536 (2007/10/02)
Asymmetric epoxidation of conjugated dienes and enynes catalyzed by (salen)Mn(II) coplex I takes place with high chemoselectivity to afford monoepoxides exclusively.Reactions of cis-enynes proceed with very high levels of asymmetric induction, with trans-alkynyl epoxides as the major products.
Regio- and Stereocontrolled Synthesis of Allenic and Acetylenic Derivatives. Organotitanium and Boron Reagents
Furuta, Kyoji,Ishiguro, Masaharu,Haruta, Ryuichi,Ikeda, Nobuo,Yamamoto, Hisashi
, p. 2768 - 2776 (2007/10/02)
The propargyltitanium reagents derived from 1-alkylpropyne condensed with aldehydes to give α-allenyl alcohol regioselectively, while the allenyltitanium reagents generated from 1-alkyl-1-butyne derivatives gave threo-β-acetylenic alcohols with high regio- and stereoselectivities.The course of the reaction was determined by the substitution pattern of starting alkynes.The similar reactions of metallated 1,3-bis(trialkylsilyl)propyne or (trialkylsilyl)acetonitrile with aldehydes were also investigated.
Propargylic Titanium Reagents. Regio- and Stereocontrolled Synthesis of Allenic and Acetylenic Alcohols
Ishiguro, Masaharu,Yamamoto, Nobuo Ikeda Hisashi
, p. 2225 - 2227 (2007/10/02)
The highly selective condensations of propargylic titanium reagents and aldehydes are described.
