99945-63-8

Upstream product

• 87172-27-8 cis-4-benzyloxy-2,3-epoxy-1-butanol 
• 69152-87-0 4-benzyloxycrotonaldehyde 
• 69152-87-0 4-benzyloxybut-2-enal 
• 78513-08-3 (2S,3R)-p-nitrobenzoesaeure-(4-benzyloxy-2,3-epoxy-1-butyl)ester 
• 78513-07-2 ((2R,3S)-3-((benzyloxy)methyl)oxiran-2-yl)methanol 
• 100-39-0 benzyl bromide 
• 81028-03-7 (Z)-4-benzyloxy-but-2-en-1-ol 

Downstream Products

• 113123-28-7 (S)-1-((2R,3S)-3-Benzyloxymethyl-oxiranyl)-ethanol 
• 113123-28-7 (R)-1-((2R,3S)-3-Benzyloxymethyl-oxiranyl)-ethanol 
• 142991-34-2 (2R,3R,4R)-1-Benzyloxy-3-bromo-pentane-2,4-diol 
• 142991-35-3 (2S,3R,4R)-5-Benzyloxy-4-chloro-pentane-2,3-diol 
• 113123-34-5 (R)-1-((2S,3R)-3-Benzyloxymethyl-oxiranyl)-but-3-en-1-ol 
• 99883-94-0 (2S,3S)-4-(benzyloxy)-1,1-dimethoxy-2,3-epoxybutane 

Relevant academic research and scientific papers

Synthesis of Phostones via the Palladium-Catalyzed Ring Opening of Epoxy Vinyl Phosphonates

The reaction of epoxy aldehydes with tetraethyl methylenediphosphonate gave γ,δ-epoxy vinyl phosphonates. The palladium-catalyzed addition of primary alcohols gave the monoprotected diols as single diastereoisomers. The trans- and cis-epoxides lead to opp

Organocatalytic asymmetric epoxidation and tandem epoxidation/Passerini reaction under eco-friendly reaction conditions

An eco-friendly synthesis of highly functionalized epoxides and their incorporation into an organocatalytic multicomponent approach are reported. For this, a modified class of diarylprolinol silyl ethers was designed to enable high catalytic activity in an environmentally benign solvent system. The one-pot procedure showed great efficiency in promoting stereoselective multicomponent transformations in a tandem, 'green' fashion. Because of its non-residual, efficient and selective character, this synthetic design shows promise for large-scale applications in both diversity and target-oriented syntheses. The Royal Society of Chemistry 2012.

Asymmetric formal trans -dihydroxylation and trans -aminohydroxylation of α,β-unsaturated aldehydes via an organocatalytic reaction cascade

This study demonstrates the first formal asymmetric trans-dihydroxylation and trans-aminohydroxylation of α,β-unsaturated aldehydes in an organocatalytic multibond forming one-pot reaction cascade. This efficient process converts α,β-unsaturated aldehydes into optically active trans-2,3-dihydroxyaldehydes and trans-3-amino-2-hydroxyaldehydes with the aldehyde moiety protected as an acetal. The elaborated one-pot protocol proceeds via the formation of 2,3-epoxy and 2,3-aziridine aldehyde intermediates, which subsequently participate in a novel NaOMe-initiated rearrangement reaction leading to the formation of acetal protected trans-2,3-dihydroxyaldehydes and trans-3-amino-2-hydroxyaldehydes in a highly stereoselective manner. Advantageously, this multibond forming reaction cascade can be performed one-pot, thereby minimizing the number of manual operations and purification procedures required to obtain the products. Additionally, for the purpose of trans-aminohydroxylation of the α,β-unsaturated aldehydes, a new enantioselective aziridination protocol using 4-methyl-N-(tosyloxy) benzenesulfonamide as the nitrogen source has been developed. The mechanism of the formal trans-dihydroxylation and trans-aminohydroxylation of α,β-unsaturated aldehydes is elucidated by various investigations including isotopic labeling studies. Finally, the products obtained were applied in the synthesis of numerous important molecules.

Mukaiyama aldolisation reactions of α,β-epoxyaldehydes in aqueous media

The Mukaiyama aldolisation reaction in aqueous media of cis and trans α,β-epoxyaldehydes with tert-butyldimethylsilyl ketene acetal in the presence of Lewis's acids was studied. Sc(OTf)3 gave the best results in terms of selectivity. The same r

Palladium-catalyzed stereospecific epoxide-opening reaction of γ,δ-epoxy-α,β-unsaturated esters with an alkylboronic acid leading to γ,δ-vicinal diols with double inversion of the configuration

A palladium-catalyzed stereospecific epoxide-opening reaction of γ,δ-epoxy-α,β-unsaturated esters with an alkylboronic acid leading to γ,δ-vicinal diols is described, which proceeds with retention of the configuration, i.e., via two consecutive SN/s

A study on the chelation control in the regioselective opening of 2,3-bifunctionalized epoxides

The results obtained in the MgBr2-mediated opening of 2,3-bifunctionalized epoxides are reported. The studies showed that the chelation control of MgBr2 between different functionalities can in some cases be selective.

Aminolysis of vinyl epoxides as an efficient entry to N-H vinylaziridines

Vinyl epoxides 8a-f 11 and 12 have been prepared from the corresponding epoxy alcohols while 8g was formed by a regioselective epoxidation of the parent diene. Aminolysis of these materials resulted in a regio- and stereoselective nucleophilic opening at C3 in good yields except for the sterically hindered substrates. The trans-oxiranes gave the anti-amino alcohols while the cis derivative 12 gave the syn isomer 17. Cyclization of the anti-amino alcohols was best effected using the Mitsunobu protocol giving the corresponding N-H vinylaziridines in 50-54% yields, while the syn-amino alcohol 17 was transformed into the cis-vinylaziridine 31 with chlorosulfonic acid followed by base treatment in 20% yield. The outcome of these cyclizations seems to indicate that they are controlled by subtle steric effects in the substrate. The N-H vinylaziridine 24 was alkylated with tert-butyl bromoacetate and the product subjected to an aza[2,3]-Wittig rearrangement to give tetrahydropyridine 30 while acetylation of 24 followed by base treatment resulted in an aza-[3,3]-Claisen rearrangement yielding the seven-membered lactam 32.

A highly efficient practical method for the synthesis of chiral polyhydroxy-(E,E)-1-chlorodienols and (E)-5-hydroxy enynes

An efficient protocol for the synthesis of chiral polyhydroxy-(E, E)-1-chlorodienols and (E)-5-hydroxy enynes from chiral 4,5-epoxy trans allyl chlorides and 4,5-O-isopropylidene allyl chlorides is described by using stoichiometric amount of LiNH2 or LDA in HMPA : THF (1 : 5) useful in the synthesis of biologically active natural products.

Alkylative Elimination of α,β-Epoxy Tosylhydrazones

Optically pure allyl alcohols have been prepared from tosylhydrazones derived from chiral epoxy aldehydes by alkylative elimination utilizing alkyl magnesium reagents.

HIGHLY REGIOSELECTIVE PALLADIUM-MEDIATED SUBSTITUTION OF ALLYLIC AND DIENYLIC CYCLIC CARBONATES

Reaction of chiral allylic and dienylic cyclic carbonates with various nucleophiles in the presence of (PPh3)4Pd as a catalyst afforded α-, γ-, or ε-substituted products with high regio-, (E)-stereo-, and diastereoselectivity depending on nucleophiles.