87506-22-7

Upstream product

• 59376-64-6 (2E)-3-(trimethylsilyl)prop-2-en-1-ol 
• 62861-80-7 (Z)-3-(trimethylsilyl)-2-propen-1-ol 
• 5272-36-6 3-trimethylsilyl-2-propyn-1-ol 
• 558-13-4 carbon tetrabromide 

Downstream Products

• 144512-07-2 {(E)-2-[(2R,3R)-3-(4-Chloro-phenyl)-oxiranyl]-vinyl}-trimethyl-silane 
• 144512-07-2 {(E)-2-[(2S,3R)-3-(4-Chloro-phenyl)-oxiranyl]-vinyl}-trimethyl-silane 
• 144512-10-7 [(E)-2-((2R,3R)-3-Biphenyl-4-yl-oxiranyl)-vinyl]-trimethyl-silane 
• 144512-10-7 [(E)-2-((2S,3R)-3-Biphenyl-4-yl-oxiranyl)-vinyl]-trimethyl-silane 
• 144512-08-3 {(E)-2-[(2S,3R)-3-(4-Bromo-phenyl)-oxiranyl]-vinyl}-trimethyl-silane 
• 144512-08-3 {(E)-2-[(2R,3R)-3-(4-Bromo-phenyl)-oxiranyl]-vinyl}-trimethyl-silane 
• 144512-11-8 [(E)-2-((2R,3R)-3-Cyclohexyl-oxiranyl)-vinyl]-trimethyl-silane 
• 144512-11-8 [(E)-2-((2S,3R)-3-Cyclohexyl-oxiranyl)-vinyl]-trimethyl-silane 
• 144512-14-1 [(E)-2-(3,3-Diphenyl-oxiranyl)-vinyl]-trimethyl-silane 
• 84673-81-4 Triphenylphosphoniumbromid 

Relevant academic research and scientific papers

An Aliphatic Bischler-Napieralski Reaction: Dihydropyridones by Cyclocarbonylation of 3-Allylimidazolidin-4-ones

The N-chloroformylimidazolidinone derivative of enantiopure l-alanine was deprotonated to form an enolate and functionalized with a series of allylic halides. Treatment of the resulting carbamoyl chlorides with potassium iodide led to cyclization of the allylic substituent onto the carbonyl group in an intramolecular aliphatic Friedel-Crafts-type acylation that corresponds to an aliphatic Bischler-Napieralski reaction. The product 3,4-dihydropyridinones were amenable to further functionalization, and finally hydrolysis, to deliver a series of enantio-enriched pipecolic acid derivatives.

Expedient access to branched allylic silanes by copper-catalysed allylic substitution of linear allylic halides

An unprecedented copper-catalysed allylic transposition enables the regioselective synthesis of branched allylic silanes from linear allylic halides through direct C-Si bond formation.

Preparation of enantiomerically pure 9-azabicyclo[3,3,1]nonene derivatives. Stereochemical requirements of vinyl- and allylsilanes in iminium ion initiated cyclization

Asymmetric synthesis of the 9-azabicyclo[3,3,1]nonene skeleton of granatanine has been achieved through the cyclization of non-racemic (Z)-vinylsilane oxazolidine (Z)-2, an iminium ion precursor. The corresponding (E)-isomer (E)-2 did not cyclize in the s

A convenient and stereoselective synthesis of trimethylsilylvinyl oxiranes via silylated telluronium allylide+

Trimethylsilylated diisobutyltelluronium allylide, a moderately stabilized telluronium ylide, generated from 3-trimethylsilyl-2-propenyldiisobutyltelluronium bromide (3) with LiTMP, reacted with carbonyl compounds to afford trimethylsilylvinyl oxiranes in excellent yields with high syn stereoselectivity.

Wittig Rearrangement-Peterson Olefination Sequence: A Stereocontrolled Entry to Terminal Conjugated Trienes

A new and highly stereocontrolled entry to terminal conjugated trienes is described which relies upon the diastereoselective Wittig rearrangement of γ-(silyl)allylic propargyl ethers followed by Peterson olefination.The synthetic utility of this meth

ENANTIOSELECTIVE SYNTHESIS OF THE NAGILACTONE RING SYSTEM VIA VINYLSILANE-MEDIATED POLYENE CYCLIZATION.

The functionalized tricyclic nagilactone precursor 19 was synthesized by a route featuring a vinylsilane terminated/1,3-dioxane acetal initiated bicyclization.Relative and absolute stereochemical control were achieved via the optically active pentenolide template 14.

A novel synthetic route to 6-azabicyclooct-3-enes via silicon directed N-acyliminium chemistry. Synthesis of (+/-)-gabaculine

Alkylation of the lithium enolate, derived from 5-ethoxy-2-pyrrolidone 1 (Scheme 1), using alkyl halides containing either the vinylsilane or 2-propynylsilane moiety, provides substrates 3 for cyclization studies passing through N-acyliminium intermediate

REGIOSELECTIVE SYNTHESIS OF (+/-)-GABACULINE

(+/-)-Gabaculine has been synthesized via an intramolecular reaction of an N-acyliminium intermediate with a propargyl silane, followed by allene ozonolysis and a Shapiro reaction.

Silylalkenes and -dienes via (Silylalkylidene)phosphoranes

The reaction of the (silylalkylidene)phosphoranes 3 and 4 with the ketones 5 - 7 and 16 leads to the silylated olefins 8 - 10 and 17, 18.With fluorenone (11), 3 affords the spiro compound 14, via (silylpropylidene)fluorene 13, which is also obtained by dehydration of 9--9-fluorenol (12).With the ketones 5 - 7 and 11, triphenylphosphorane (20) yields the silylated dienes 21 - 24.From cyclohexane (22) and tetracyanoethene (25) the spiran 26 is formed by cycloaddition.