87938-26-9

Upstream product

• 53346-05-7 2-(benzyloxy)propanal 
• 24850-33-7 allyltributylstanane 
• 107-18-6 allyl alcohol 
• 762-72-1 allyl-trimethyl-silane 
• 184897-18-5 2-Benzyloxy-4-bromo-hex-5-en-3-ol 
• 2040-44-0 ethyl 2-benzyloxypropionate 
• 100-39-0 benzyl bromide 
• 1730-25-2 allylmagnesium bromide 

Relevant academic research and scientific papers

Mediation of the Reactivity of the Strong Lewis Acid TiCl4 by Complexation with XPh3

Lewis acid-base combinations TiCl4*XPh3 (X = As,Sb,Bi) have been developed to mediate the Lewis acidity of TiCl4.The inverse addition of TiCl4*AsPh3 to 2-(benzyloxy)propanal (1) and allylstannane 2 provided a chelation-controlled product 3 with high diast

Gold(I)-Catalyzed Intramolecular Dehydrative Amination of Sulfamate Esters Tethered to Allylic Alcohols: A Strategy for the Synthesis of Cyclic Sulfamidates

An efficient synthesis protocol for cyclic sulfamidates has been developed via catalytic intramolecular cyclizations of sulfamate esters tethered to allylic alcohols. The reactions proceed smoothly at room temperature in the presence of (IPr)AuCl (5 mol%) and AgBF4 (5 mol%). This protocol features good to excellent yields, high selectivity, broad substrate scope, and mild reaction conditions. This method is also applicable to the synthesis of a seven-membered sulfamidate. (Figure presented.).

Stereoselective Reactions of Phthalimido-Substituted Radicals Derived from (±)-Threonine: A Comparison with Reactions of N-Phthaloyliminium Ions

Stereoselective reactions of phthalimido-substituted radicals derived from (±)-threonine with different radical traps are reported (Scheme 3, Table 1). A strong influence of the nature of the radical trap on the stereoselectivity was noticed. Small nucleophilic radical traps gave preferentially the syn products. The observed selectivities are explained with the A1.3 strain model and depend on steric and electronic effects (Fig. 2). Reactions with electrophilic radical traps such as diphenyl diselenide gave the anti diastereoisomers with moderate stereocontrol, presumably due to stereoelectronic effects. The same stereochemical outcome, i.e., preferential formation of the anti products, was observed for the reactions of the related N-phthaloyliminium ion (Scheme 5, Table 2). The stereochemistry of the ionic reaction is rationalized by a Felkin-Anh model (Fig. 3).

Comparative Diastereoselectivity Analysis of Crotylindium and 3-Bromoallylindium Additions to a-Oxy Aldehydes in Aqueous and Nonaqueous Solvent Systems

The couplings of crotyl bromide (1) and 1,3-dibromopropene (2) to a triad of conformationally unrestricted α-oxy aldehydes in water, aqueous THF (1:1), and anhydrous THF are described. In no example involving 1 was the formation of anti.syn product detected. The proportion of syn isomers reached a maximum (syn/anti = 5.6:1) when the neighboring hydroxyl group was unprotected and water was the reaction medium. Although internal chelation also operates to some degree with 2, considerable erosion of this mechanistic pathway (maximum now only 2:1) in favor of Felkin and "anti-Felkin" transition states is reflected in the product distributions. This trend can be synthetically advantageous, and a utilitarian example is demonstrated. The indium reagents studied here are notably efficient nucleophilic reaction partners in water.

Palladium-Catalyzed Carbonyl Allylation of Diketo Compounds by Allylic Alcohols with SnCl2

Palladium-catalyzed diallylation of 1,2-diketones and 1,2-ketoaldehyde by allylic alcohol with SnCl2 in DMI was accelerated and proceeded diastereoselectively thanks to a chelation of a carbonyl group to Sn(IV) (tin alkoxide) in the corresponding monoallylated intermediates.

Acyclic Stereoselection. 22. Diastereofacial Selectivity in the Lewis Acid Mediated Reactions of Allylsilanes with Chiral Aldehydes and Enones

The Lewis acid mediated reactions of chiral aldehydes 1-4 and enones 5-8 with allylsilanes 9 and 10 have been investigated.With aldehyde 1 and enones 5-7, modest diastereofacial preferences are seen, in the sense predicted by application of Felkin's model for asymmetric induction.Aldehydes 2-4 and enone 8 appear to react by way of chelated intermediates.With these four compounds, the diastereofacial preferences are rather large and are in the sense that is consistend with attack of the allylsilane on the least hindered face of the chelated intermediate.In the reaction of the trans and cis enones 6 and 8 with allyltrimethylsilane, a dramatic reversal of diastereofacial preference is observed; enone 6 gives a 84:14 ratio of products, while enone 8 provides a 10:90 mixture of the same products.