81850-16-0

Upstream product

• 627-40-7 methylallylether 
• 100-52-7 benzaldehyde 
• 110388-17-5 (E)-γ-(methoxyallyl)tributylstannane 
• 77896-96-9 2-<(Z)-3-methoxy-2-propenyl>-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 6044-68-4 3,3-dimethoxyprop-1-ene 
• 77896-97-0 2-<(E)-3-methoxy-2-propenyl>-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Downstream Products

• 19261-14-4 1-phenylbut-3-ene-1,2-diol 

Relevant academic research and scientific papers

Stereoselective Acyclic Synthesis via Allylmetals: Vicinal Diols from γ-Alkoxyallylaluminium Compounds and Aldehydes or Ketones

The reaction of in situ generated γ-alkoxyallylaluminium compounds with aldehydes or ketones at -78 deg C leads to the highly diastereoselective formation of mono-protected vicinal diols; the precursor to exo-brevicomin was efficiently synthesised using t

Catalytic Allylation of Aldehydes Using Unactivated Alkenes

Simple feedstock organic molecules, especially alkenes, are attractive starting materials in organic synthesis because of their wide availability. Direct utilization of such bulk, inert organic molecules for practical and selective chemical reactions, however, remains limited. Herein, we developed a ternary hybrid catalyst system comprising a photoredox catalyst, a hydrogen-atom-transfer catalyst, and a chromium complex catalyst, enabling catalytic allylation of aldehydes with simple alkenes, including feedstock lower alkenes. The reaction proceeded under visible-light irradiation at room temperature and with high functional group tolerance. The reaction was extended to an asymmetric variant by employing a chiral chromium complex catalyst.

Ni- and pd-catalyzed synthesis of substituted and functionalized allylic boronates

Two highly efficient and convenient methods for the synthesis of functionalized and substituted allylic boronates are described. In one procedure, readily available allylic acetates are converted to allylic boronates catalyzed by Ni/PCy3 or Ni/PPh3 complexes with high levels of stereoselectivity and in good yields. Alternatively, the borylation can be accomplished with commercially available Pd catalysts [e.g., Pd 2(dba)3, PdCl2, Pd/C], starting with easily accessed allylic halides.

Cytochrome P450-catalyzed hydroxylation of mechanistic probes that distinguish between radicals and cations. Evidence for cationic but not for radical intermediates

Oxidation of the mechanistic probes trans,trans-2-methoxy-3- phenylmethylcyclopropane and methylcubane by six cytochrome P450 isozymes has been studied. The probes differentiate between radical and cationic species in that different structural rearrangeme

Bu4NF-BF3*Et2O as a New Reagent for the Selective Deprotection of the Enol Ethers of γ-Alkoxyallylstannanes

The combination of Bu4NF-BF3*Et2O deprotects selectively the enol ether protecting group of γ-alkoxy- and benzyloxy-allyltributylstannanes, without destannylating the tributylstannyl group, affording the corresponding γ-tributylstannyl aldehyde in high yield.

REDUCTION OF ACROLEIN DIALKYL ACETALS WITH CrCl2. γ-ALKOXY SUBSTITUTED ALLYLIC CHROMIUM REAGENTS FOR SELECTIVE SYNTHESIS OF erythro-1,2-DIOLS.

Treatment of an aldehyde in THF at -30 deg C with a reagent derived by reduction of acrolein dialkyl acetal with CrCl2 in the presence of Me3SiI gave 1,2-erythro-3,4-butene-1,2-diol derivatives selectively.

Stereoselective Synthesis of Alcohols, XX. - Diastereoselective Addition of γ-Alkoxyallylboronates to Aldehydes

Both the (Z)- and (E)-γ-alkoxysubstituted allylboronates 1 and 3 have been prepared.They add to aldehydes with a diastereoselectivity generally exceeding 90percent to give the syn-(2) and anti-diol derivatives 4, respectively.The structure of one of these adducts has been established by conversion into exo-brevicomin (26).

DIASTEREOSELECTIVE ADDITION OF γ-METHOXY-ALLYLBORONATES TO ALDEHYDES

The E- and Z-γ-methoxy-allylboronates 1 and 3 add cleanly to aldehydes to give diastereoselectively the adducts 2 and 4.