52149-13-0

Upstream product

• 4784-77-4 (E/Z)-crotyl bromide 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 18292-28-9 1-(trimethylsilyl)but-2-ene 
• 52922-10-8 2-methyl-1-phenyl-3-buten-1-ol 
• 74-88-4 methyl iodide 
• 75851-67-1 4,4,5,5-tetramethyl-2-(1-methyl-2-propenyl)-1,3,2-dioxaborolane 
• 69611-01-4 (Z)-2-(but-2-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 69611-02-5 (E)-2-(but-2-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 35998-93-7 tri-n-butylcrotyltin 
• 3200-73-5 trans-2-butenyltrimethylstannane 
• 52922-10-8 (1SR,2SR)-2-methyl-1-phenylbut-3-en-1-ol 
• 63553-62-8 (1S*,2R*)-2-methyl-1-phenylbut-3-en-1-ol 
• 17486-13-4 (Z)-crotyltrimethylsilane 
• 35364-99-9 α-chlorobenzyl methyl ether 

Relevant academic research and scientific papers

Unusual carbon-carbon bond formations between allylboronates and acetals or ketals catalyzed by a peculiar indium(I) lewis acid

InIOTf has been uncovered as an effective Lewis acid catalyst for unprecedented nucleophilic substitution of acetals or ketals with allylboronates. A transmetalative SN1 mechanism is proposed in which a single InI center acts as a dual catalyst to activate both reagents sequentially. Contrary to the classic γ-selectivity of allylsilanes (Hosomi-Sakurai reaction), this InI-catalyzed borono variant displays distinct α-selectivity. Substrate scope and functional group tolerance proved to be excellent.

Homogeneous Catalysis. Use of the Catalyst for the Sakurai Reaction of Allylic Silanes with Orthoesters, Acetals, Ketals and Carbonyl Compounds.

The effectiveness of the catalyst for the Sakurai reaction has been explored for a variety of allylic silanes reacting with orthoesters, acetals, ketals, aldehydes and ketones. Key Words: Sakurai reaction, titanium based catalyst.

TRIMETHYLSILYL TRIFLATE CATALYZED ALDOL-TYPE REACTION OF ENOL SILYL ETHERS AND ACETALS OR RELATED COMPOUNDS

Trimethylsilyl triflate with or without added hindered tertiary amines catalyzes directed condensation of enol trimethylsilyl ethers with acetals, orthoformate, or 2-acetoxytetrahydrofuran or -pyrans to give the corresponding β-alkoxy carbonyl compounds.R

METHOXY(PHENYLTHIO)METHANE AS AN AMBI-EQUVIVALENT OF A METHOXY- OR PHENYLTHIOMETHYLENE 1,1-DIPOLE

Methoxy(phenylthio)methane undergoes electrophilic alkylation followed by nucleophilic allylation or propargylation which is dramatically changed depending on the Lewis acid employed providing a methoxy- or phenylthiomethylene 1,1-dipole synthon.

DIASTEREOSELECTIVE REACTION OF CROTYLSILANES WITH ACETALS. IMPORTANCE OF THE ELECTRONIC EFFECT IN ACYCLIC STEREOSELECTION

Acyclic stereoselection of aromatic acetals in the reaction with crotylsilanes depends upon the geometry of crotylsilanes.It was also disclosed for the first time that the electronic effect plays an important role on controlling the diastereochemistry.

A FACILE SYNTHESIS OF HOMOALLYL ETHERS. THE REACTION OF ACETALS WITH ALLYLTRIMETHYLSILANES PROMOTED BY TRITYL PERCHLORATE OR DIPHENYLBORYL TRIFLATE

In the presence of a catalytic amount of trityl perchlorate or diphenylboryl triflate, acetals react smoothly with allyltrimethylsilanes to give the corresponding homoallyl ethers in good yields with good regio- and stereoselectivities.

STEREO- AND REGIOCONTROL OF ACYCLIC SYSTEMS VIA THE LEWIS ACID MEDIATED REACTION OF ALLYLIC STANNANES WITH ALDEHYDES

The reaction of crotyltrialkylstannanes (1) with aldehydes in the presence of BF3*OEt2 produces the corresponding erythro homoallyl alcohols (2) predominantly regardless of the geometry of the double bond. Further, the Lewis acid mediated reaction exhibits the enhanced Cram selectivity in comparison with other allylic organometallic reactions which proceed in the absence of Lewis acids.Use of AlCl3-i-PrOH as the Lewis acid entirely changes the reaction course; the linear adduct (12) is produced rather than the branched adduct (13).The reaction of 1-BF3*OEt2 system is applied to the short and stereoselective synthesis of the (+/-) Prelog-Djerassi lactonic acid (16) and (-) verrucarinolactone (19).

REGIOSPECIFIC ALLYLATION OF ACETALS WITH ALLYLSILANES CATALYZED BY IODOTRIMETHYLSILANE. SYNTHESIS OF HOMOALLYLETHERS

Allylation of acetals with allylsilanes is catalyzed by iodotrimethylsilane to give the corresponding homoallyl ethers, with regiospecific transposition of the allyl group.