321882-80-8

Upstream product

• 292638-85-8 acrylic acid methyl ester 
• 615574-37-3 (4R,5R)-4,5-Bis-(methoxy-diphenyl-methyl)-2-((1R,2R)-2-vinyl-cyclopropyl)-[1,3,2]dioxaborolane 
• 321882-78-4 (4R,5R,1'R,2'R)-2-[2-(hydroxymethyl)cyclopropyl]-4,5-bis[methoxy(diphenyl)methyl]-1,3,2-dioxaborolane 
• 5927-18-4 trimethyl phosphonoacetate 
• 321882-79-5 (1R,2R)-2-[(4R,5R)-4,5-Bis-(methoxy-diphenyl-methyl)-[1,3,2]dioxaborolan-2-yl]-cyclopropanecarbaldehyde 

Downstream Products

• 321882-83-1 (4R,5R,1'R,2'R,1''S,2''R)-2-{2-[2-(tert-butyldiphenylsilyloxymethyl)cyclopropyl]cyclopropyl}-4,5-bis(methoxydiphenylmethyl)-1,3,2-dioxaborolane 
• 321882-89-7 (4R,5R,1'R,2'R,1''S,2''R)-2-{2-[2-(benzyloxymethyl)cyclopropyl]cyclopropyl}-4,5-bis(methoxydiphenylmethyl)-1,3,2-dioxaborolane 
• 321882-85-3 (1S,2R,1'R,2'R)-2'-[(4R,5R)-4,5-Bis-(methoxy-diphenyl-methyl)-[1,3,2]dioxaborolan-2-yl]-bicyclopropyl-2-carboxylic acid 
• 321882-82-0 (4R,5R,1'R,2'R,1''S,2''R)-2-{2-[2-hydroxymethylcyclopropyl]cyclopropyl}-4,5-bis(methoxydiphenylmethyl)-1,3,2-dioxaborolane 
• 321882-84-2 (1'R,2'R,1''S,2''R)-2-{2-[2-(tert-butyldiphenylsilyloxymethyl)cyclopropyl]cyclopropyl}-1,3,2-dioxaborinane 
• 321882-90-0 (1'R,2'R,1''S,2''R)-2-{2-[2-(benzyloxymethyl)cyclopropyl]cyclopropyl}-1,3,2-dioxaborinane 
• 178602-56-7 (1'R,2'R,1''S,2''R)-2-{2-[2-(tert-butyldiphenylsilyloxymethyl)cyclopropyl]cyclopropyl}methanol 
• 130874-89-4 (2R,3R)-1,4-dimethoxy-1,1,4,4-tetraphenyl-2,3-butandiol 
• 321882-81-9 (1'R,2'R,4R,5R)-2-{2-[(E)-2-hydroxymethylethenyl]cyclopropyl}-4,5-bis(methoxydiphenylmethyl)-1,3,2-dioxaborolane 

Relevant academic research and scientific papers

Synthesis of enantiomerically pure vinylcyclopropylboronic esters via cross-metathesis

The potent antibiotic ambruticin caused us to investigate two new aspects of cyclopropylboronic ester chemistry: we established the analytical basics for all 1,2,3-trisubstituted diastereoisomers as well as the cross-metathesis as a tool to synthesise vinylcyclopropylboronic esters.

Enantiomerically Pure Vinylcyclopropylboronic Esters

Vinylcyclopropanes are versatile intermediates and products in organic synthesis. The corresponding enantiomerically pure boronic esters should lead to highly flexible building blocks with a variety of applications. A detailed study towards the selective

(2R,3R)-1,4-Dimethoxy-1,1,4,4-tetraphenyl-2,3-butanediol: Chiral auxiliary and efficient protecting group for boronic acids

(2R,3R)-1,4-Dimethoxy-1,1,4,4-tetraphenyl-2,3-butanediol (1) has been used as an efficient chiral auxiliary in the cyclopropanation of alkenylboronic esters. The stability of the obtained cyclopropylboronic esters allowed the chromatographic separation of the diastereoisomers. Furthermore, it enabled a variety of transformations in the side-chain, including oxidation, reduction, and reactions under acidic, basic, or radical conditions, that finally led to boron containing functionalized bicyclopropanes, e.g., 12 and 18. The absolute configurations of these building blocks were established by X-ray crystallography (compound 10) and by chemical correlation. The Matteson homologation led to a known advanced intermediate of the oligocyclopropane FR-900848.