128574-72-1

Upstream product

• 27686-42-6 trans-bis(o-iodophenyl)ethylene 
• 52340-78-0 (R,R)-hydroxybenzoin 
• 62680-65-3 (2-iodobenzyl)triphenylphosphonium bromide 
• 26260-02-6 2-iodobenzaldehyde 

Downstream Products

• 1146729-46-5 (4R,5R)-4,5-bis-(2-iodophenyl)-2,2-dimethyl-1,3-dioxolane 
• 1352150-95-8 (1R,2R)-1,2-dimethoxy-1,2-bis(2-iodophenyl)ethane 
• 1146729-48-7 (4R,5R)-4,5-bis-(biphenyl-2-yl)-2,2-dimethyl-1,3-dioxolane 
• 1041002-83-8 (4R,5R)-4,5-bis-(2-trimethylsilylphenyl)-2,2-dimethyl-1,3-dioxolane 

Relevant academic research and scientific papers

Directed ortho,ortho'-dimetalation of hydrobenzoin: Rapid access to hydrobenzoin derivatives useful for asymmetric synthesis

A variety of ortho,ortho'-disubstituted hydrobenzoin derivatives are readily accessible through a directed ortho,ortho'-dimetalation strategy in which the alcohol functions in hydrobenzoin are deprotonated by n-BuLi and the resulting lithium benzyl alkoxi

Bidirectional metalation of hydrobenzoin: Direct access to new chiral ligands and auxiliaries

A bidirectional ortho metalation of the readily available chiral diol hydrobenzoin has been developed that provides direct access to new ortho-functionalized hydrobenzoin derivatives. This one-pot procedure should broaden the utility of hydrobenzoin as an

Catalytic enantioselective allyl- and crotylboration of aldehydes using chiral diol·SnCl4 complexes. Optimization, substrate scope and mechanistic investigations

We report a novel class of C2-symmetric chiral diols derived from the hydrobenzoin skeleton. The combination of these diols with SnCl 4 under Yamamoto's concept of Lewis acid assisted Bronsted acidity (LBA catalysis) leads to high levels of asymmetric induction in the allylboration of aldehydes by commercially available allylboronic acid pinacol ester 1a. The corresponding homoallylic alcohol products of synthetically useful aliphatic aldehydes are obtained in excellent yields with up to 98:2 er. This combined acid manifold is also efficient in catalyzing the diastereo- and enantioselective crotylboration of aldehydes, thus providing the propionate units in >95:5 dr and up to 98:2 er. The X-ray crystal structure of the optimal diol·SnCl4 complex, Vivol (4m)·SnCl 4, unambiguously shows the Bronsted acidic character of this LBA catalyst and its highly dissymmetrical environment. Further controls have ruled out a possible boron transesterification mechanism with the chiral diol and point to LBA catalyst-derived activation of the pinacol allylic boronates 1. Due to slow dissociation of the diol·SnCl4 complex, a small excess of diol is required in order to suppress a competing racemic cycle catalyzed by free SnCl4.

Intramolecular biaryl coupling: asymmetric synthesis of the chiral B-ring unit of pradimicinone

The combination of palladium-catalyzed intramolecular biaryl coupling with enantioselective dihydroxylation of achiral stilbenes provides an efficient, two-step route to the chiral 9,10-dihydrophenanthrenediol unit of the pradimicins and benanomicins.