133321-92-3

Upstream product

• 18295-60-8 allenylmagnesium bromide 
• 2043-61-0 cyclohexanecarbaldehyde 
• 1178609-34-1 (1S,2S,4'R,5'R)-2-[4',5'-bis(methoxydiphenylmethyl)-1',3',2'-dioxaborolan-2'-yl]-1-cyclohexylbut-3-en-1-ol 
• 106948-15-6 {[(R)-1-((S)-Cyclohexyl-trimethylsilanyloxy-methyl)-allyl]-dimethyl-silanyl}-diisopropyl-amine 
• 133321-84-3 (4R,5R)-2-[(E)-3-(Cyclohexyloxy-dimethyl-silanyl)-allyl]-[1,3,2]dioxaborolane-4,5-dicarboxylic acid diisopropyl ester 
• 135340-32-8 (-)-B-<3-(diisopropylaminodimethylsillyl)allyl>diisopinocampheylborane 
• 133285-45-7 (1R,2S)-1-cyclohexyl-2-(cyclohexyloxydimethyl)silylbut-3-ene-1-ol 

Relevant academic research and scientific papers

B-diisopinocampheylborane: An Excellent Reagent for the Stereoselective Synthesis of Anti Vicinal Diols

Aldehydes reacted stereoselectively with B-diisopinocampheylborane, derived from (+)- and (-)-α-pinene, to provide, on workup with hydrogen peroxide, (3S,4R)- and (3R,4S)-dihydroxy-1-alkenes, respectively.

Palladium-catalyzed synthesis of enantiomerically pure α-substituted allylboronic esters and their addition to aldehydes

Tartrate-derived boronic esters 2 can be subjected to palladium-catalyzed carbonyl allylations with SnCl2 to obtain enantiomerically pure α-substituted allylboronic esters 8 and 9. The reaction proceeds regioselectively and with high, simple diastereoselectivity to form anti-products. Their addition to aldehydes yields enantiomerically enriched homoallylic alcohols 17 and 18, respectively. Synthesis, characterization, and a mechanistic rational is presented here.

3-bromozinc propenyl esters: An experimental and theoretical study of the unique stereocrossover observed in their addition to aromatic and aliphatic aldehydes

(Chemical Equation Presented) We report the results of a combined experimental and theoretical study on the reaction of 3-bromopropenyl acetate in the presence of zinc with three different aldehydes (i.e., benzaldehyde, 2-methylpropanal, and cyclohexaneca

Diisopropyl tartrate modified (E)-γ-[(cyclohexyloxy)dimethylsilyl]-and (E)-γ-(dimethylphenylsilyl)allylboronates: Chiral reagents for the enantio-and diastereoselective synthesis of anti 1,2-diols and 2-butene-1,4-diols via the formal α- and γ-hydroxyallylation of aldehydes

Enantioselective synthesis of 4-substituted (E)-2-butene-1,4-diols and anti 1,2-diols are described. Highly diastereoselective reactions of aldehydes and the chiral PhMe2Si- and (C6H11O)Me2Si-substituted allylboronates 25 and 26 provide anti homoallylic 29 and 50, respectively. Epoxidation of 29 with dimethyl dioxirane followed by acid catalyzed Petersen rearrangement of the intermediate epoxysilanols provides butee-1,4-diols 27 with excellent enantioselectivity (81-87% e.e.). Tamao oxidation of 50 provides anti diols 22 (64-72% e.e). These procedures give excellent results especially in matched double asymmetric reactions with a range of oxygenated, chiral aldehydes (Figures 1 and 2). These methods promise to find application in diastereoselective syntheses of carbohydrates from acyclic precursors.

Diisopropyl tartrate modified (E)-γ-[(cyclohexyloxy)dimethylsilyl]-allylboronate, a chiral reagent for the stereoselective synthesis of anti 1,2-diols via the formal α-hydroxyallylation of aldehydes

An enantioselective synthesis of anti 1,2-diols via the reactions of aldehydes and the tartrate ester modified γ-(alkoxysilyl)allylboronate 2 has been developed. This method is most effective in double asymmetric reactions with chiral aldehydes.

Metalated Allylaminosilane: A New, Practical Reagent for the Stereoselective α-Hydroxyallylation of Aldehydes to Erythro-1,2-diol Skeletons

A zinc reagent derived from allyl(diisopropylamino)dimethylsilane reacts with aldehydes regio- and stereoselectively to form erythro-3-silyl-1-alken-4-ols, which are further transformed into erythro-1-alkene-3,4-diols by hydrogen peroxide oxidation of the