571206-65-0

Upstream product

• 571206-58-1 (R)-3-bromo-2-phenyl-1-propanol 
• 1570-95-2 2-phenylpropane-1, 3-diol 
• 10317-13-2 3-phenyloxetane 
• 571206-57-0 C₁₆H₁₇BrO 
• 510730-52-6 (4S,2'R)-3-((2'-benzyloxymethyl)phenylacetyl)-4-(phenylmethyl)-2-oxazolidinone 
• 171617-30-4 (S)-1-benzyloxy-2-phenyl-1,3-propanediol 
• 104266-89-9 (S)-4-benzyl-3-phenylacetyl-2-oxazolidinone 

Relevant academic research and scientific papers

Highly Enantioselective, Hydrogen-Bond-Donor Catalyzed Additions to Oxetanes

A precisely designed chiral squaramide derivative is shown to promote the highly enantioselective addition of trimethylsilyl bromide (TMSBr) to a broad variety of 3-substituted and 3,3-disubstituted oxetanes. The reaction provides direct and general access to synthetically valuable 1,3-bromohydrin building blocks from easily accessed achiral precursors. The products are readily elaborated both by nucleophilic substitution and through transition-metal-catalyzed cross-coupling reactions. The enantioselective catalytic oxetane ring opening was employed as part of a three-step, gram-scale synthesis of pretomanid, a recently approved medication for the treatment of multidrug-resistant tuberculosis. Heavy-atom kinetic isotope effect (KIE) studies are consistent with enantiodetermining delivery of bromide from the H-bond-donor (HBD) catalyst to the activated oxetane. While the nucleophilicity of the bromide ion is expected to be attenuated by association to the HBD, overall rate acceleration is achieved by enhancement of Lewis acidity of the TMSBr reagent through anion abstraction.

Method for asymmetrically opening ring of 3-substituted oxetane and application

The invention discloses a method for catalytically asymmetrically opening a ring of 3-substituted oxetane by using halogen. The method comprises the following steps: with 3-substituted oxetane and a halogen nucleophile as reaction substrates, under the ac

Enantioselective Oxetane Ring Opening with Chloride: Unusual Use of Wet Molecular Sieves for the Controlled Release of HCl

An unprecedented enantioselective oxetane opening with chloride provides access to a range of highly functionalized three-carbon building blocks. The excellent enantiocontrol is enabled not only by a new catalyst, but also by the unusual use of wet molecular sieves for the controlled release of HCl. The enantioselective ring opening of oxetanes with chloride provides access to a range of highly functionalized three-carbon building blocks. The use of a new catalyst in combination with wet molecular sieves for the controlled release of HCl leads to high enantioselectivities.

Asymmetric Schmidt reaction of hydroxyalkyl azides with ketones

An asymmetric equivalent of the Schmidt reaction permits stereocontrol in ring expansions of symmetrical cyclohexanones. The procedure involves the reaction of chiral 1,2- and 1,3-hydroxyalkyl azides with ketones under acid catalysis; the initial reaction affords an iminium ether that can be subsequently opened with base. A systematic study of this reaction is reported, in which ketone substrates, chiral hydroxyalkyl azides, and reaction conditions are varied. Selectivities as high as ca. 98:2 are possible for the synthesis of substituted caprolactams, with up to 1,7-stereoselection involved in the overall process. The fact that either possible migrating carbon is electronically identical provides an unusual opportunity to study a ring-expansion reaction controlled entirely by stereoelectronic factors. The mechanism of the reaction and the source of its stereoselectivity are also discussed.