85355-87-9

Upstream product

• 13294-71-8 2-bromo-but-2-ene 
• 98-86-2 acetophenone 
• 4894-61-5 trans-but-2-enyl chloride 
• 4784-77-4 (E)-1-Bromo-2-butene 
• 22032-77-5 (E)-crotylmagnesium chloride 
• 95-14-7 1,2,3-Benzotriazole 
• 69611-01-4 (Z)-2-(but-2-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Relevant academic research and scientific papers

SmCl3-CATALYSED ELECTROCHEMICAL REDUCTIVE ALLYLATION OF KETONES

A series of homoallylic alcohols was prepared in moderate to good yields from allyl chlorides and ketones, through an electrochemical method using SmCl3 as the catalyst precursor.The electrosyntheses were carried out in undivided cells fitted with a consumable magnesium anode.

Practical, Broadly Applicable, α-Selective, Z-Selective, Diastereoselective, and Enantioselective Addition of Allylboron Compounds to Mono-, Di-, Tri-, and Polyfluoroalkyl Ketones

A practical method for enantioselective synthesis of fluoroalkyl-substituted Z-homoallylic tertiary alcohols has been developed. Reactions may be performed with ketones containing a polylfluoro-, trifluoro-, difluoro-, and monofluoroalkyl group along with an aryl, a heteroaryl, an alkenyl, an alkynyl, or an alkyl substituent. Readily accessible unsaturated organoboron compounds serve as reagents. Transformations were performed with 0.5-2.5 mol % of a boron-based catalyst, generated in situ from a readily accessible valine-derived aminophenol and a Z- or an E-?-substituted boronic acid pinacol ester. With a Z organoboron reagent, additions to trifluoromethyl and polyfluoroalkyl ketones proceeded in 80-98% yield, 97:3 to >98:2 α:? selectivity, >95:5 Z:E selectivity, and 81:19 to >99:1 enantiomeric ratio. In notable contrast to reactions with unsubstituted allylboronic acid pinacol ester, additions to ketones with a mono- or a difluoromethyl group were highly enantioselective as well. Transformations were similarly efficient and α- and Z-selective when an E-allylboronate compound was used, but enantioselectivities were lower. In certain cases, the opposite enantiomer was favored (up to 4:96 er). With a racemic allylboronate reagent that contains an allylic stereogenic center, additions were exceptionally α-selective, affording products expected from ?-addition of a crotylboron compound, in up to 97% yield, 88:12 diastereomeric ratio, and 94:6 enantiomeric ratio. Utility is highlighted by gram-scale preparation of representative products through transformations that were performed without exclusion of air or moisture and through applications in stereoselective olefin metathesis where Z-alkene substrates are required. Mechanistic investigations aided by computational (DFT) studies and offer insight into different selectivity profiles.

High regiocontrol in the zinc-mediated crotylation of aldehydes and ketones: A straightforward and facile approach to linear homoallylic alcohols in DMPU

The α-regioselectivity of carbonyl crotylation is a long-standing problem in the realm of C-C bond formation reactions. We demonstrate that zinc-mediated crotylation of aldehydes and ketones can afford α-linear homoallylic alcohols exclusively to provide

Regioselective reaction of allylbenzotriazoles with aldehydes and ketones in the presence of lithium

The reactions of α- and γ-substituted allylbenzotriazoles 2, 3 and 4 with an excess of lithium in THF at -78°C generate various allyllithiums, which react readily with aldehydes and ketones with high regioselectivity to give predominantly the branched products 5 in excellent yields.

Electrogenerated Zinc as the Catalyst in the Allylation of Carbonyl Compounds. Direct Synthesis of α-Methylene-γ-Lactones

The electroreduction of a catalytic amount of ZnBr2 in acetonitrile provided a active Zn*, able to catalyze the reductive coupling of allyl bromides and chlorides with carbonyl compounds with high regioselectivity.Substituted α-methylene γ-lactones were o

Regioreversed Addition of Crotylmagnesium Chloride to Carbonyl Compounds in the Presence of AlCl3

The reaction of carbonyl compounds with crotylmagnesium chloride in the presence of AlCl3 at -78 deg C gives predominantly products in which the allylic group is attached at the less substituted position (α-adduct).