185953-15-5

Upstream product

• 133321-84-3 (4R,5R)-2-[(E)-3-(Cyclohexyloxy-dimethyl-silanyl)-allyl]-[1,3,2]dioxaborolane-4,5-dicarboxylic acid diisopropyl ester 
• 2043-61-0 cyclohexanecarbaldehyde 
• 18295-60-8 allenylmagnesium bromide 
• 1178609-28-3 (1R,2R,4'R,5'R)-2-[4',5'-bis(methoxydiphenylmethyl)-1',3',2'-dioxaborolan-2'-yl]-1-cyclohexylbut-3-en-1-ol 
• 1374646-40-8 (S,E)-1-cyclohexyl-4-(3-nitrophenoxy)but-2-en-1-ol 
• 4352-44-7 (R)-1-cyclohexyl-prop-2-enol 

Relevant academic research and scientific papers

Iterative asymmetric allylic substitutions: Syn- and anti-1,2-diols through catalyst control

A copper-catalyzed asymmetric allylic boronation (AAB) gives access to syn- and anti-1,2-diols. The method facilitates an iterative strategy for the preparation of polyols (see scheme), such as the fully differentiated L-ribo-tetrol and protected D-arabin

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.

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.