84994-62-7

Upstream product

• 954106-46-8 C₂₇H₄₆O₆Si 
• 100-39-0 benzyl bromide 
• 80928-05-8 (R)-(+)-2-Benzyloxybutyraldehyde 
• 88376-74-3 Benzyloxy-acetic acid (1R,2S,3R,4S)-3-[benzenesulfonyl-(3,5-dimethyl-phenyl)-amino]-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 89279-49-2 2-(benzyloxy)butanal 
• 88494-65-9 (R)-2-Benzyloxy-butyric acid (1R,2S,3R,4S)-3-[benzenesulfonyl-(3,5-dimethyl-phenyl)-amino]-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester 

Relevant academic research and scientific papers

Alkylation and aldol reactions of acyl derivatives of N-1-(1′-naphthyl)ethyl-O-tert-butylhydroxylamine: asymmetric synthesis of α-alkoxy-, α-substituted-β-alkoxy- and α,β-dialkoxyaldehydes

Treatment of a range of O-protected glycolate derivatives of the chiral auxiliary N-1-(1′-naphthyl)ethyl-O-tert-butylhydroxylamine with KHMDS in the presence of 18-crown-6 followed by addition of an alkyl halide generates α-substituted derivatives with very high levels of diastereoselectivity. Alternatively, reaction of the potassium enolate of a propanoate or O-protected glycolate derivative of N-1-(1′-naphthyl)ethyl-O-tert-butylhydroxylamine with a range of aldehydes gives syn-aldol products with high levels of diastereoselectivity. These adducts may be reductively cleaved with LiAlH4 to give enantiopure α-alkoxy-, α-substituted-β-alkoxy- and α,β-dialkoxyaldehydes in good yield.

Enantioselective synthesis of chiral β-aryloxy alcohols by asymmetric hydrogenation of a-aryloxy aldehydes via dynamic kinetic resolution

A catalytic enantioselective hydrogenation of racemic α-aryloxy aldehydes via dynamic kinetic resolution has been developed by using (diamine)(spirodiphosphine)ruthenium(II) chloride [RuCl 2(SDPs)(diamine)] catalysts. Employing this new reactio

Studies toward the synthesis of pinnatoxins: the spiroimine fragment

An enantioselective approach to the spiroimine fragment of pinnatoxins is described. The strategy is based on a recently developed diastereoselective Ireland-Claisen rearrangement to establish the challenging congested quaternary and tertiary stereocenters within the cyclohexene ring.

AN ASYMMETRIC SYNTHESIS OF α-BENZYLOXY ALDEHYDES HAVING A CHIRAL TERTIARY CENTER - AN APPLICATION TO THE ASYMMETRIC SYNTHESIS OF exo-(+)-BREVICOMIN -

α-benzyloxy aldehydes having a chiral tertiary center at α-carbon atom are synthesized in high enantiomeric excess by successive treatment of 2-methoxycarbonyl-3-phenyl-1,3-diazabicyclooctane with diisobutylaluminum hydride (DIBAL-H) and Grignard reagents.The asymmetric reaction is applied to the total synthesis of exo-(+)-brevicomin.