90410-14-3

Upstream product

• 873-67-6 benzonitrile oxide 
• 62214-38-4 (S)-1,2-O-isopropylidene-but-3-ene-1,2-diol 
• 698-16-8 benzohydroximoyl chloride 
• 201596-16-9 (4''S)-2-[(E)-2-(2,2-Dimethyl-1,3-dioxolan-4-yl)ethenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 83968-02-9 2,2-dimethyl-4-vinyl-1,3-dioxolane 
• 92287-44-0 3-phenyl-5-vinyl-4,5-dihydroisoxazole 
• 77-76-9 2,2-dimethoxy-propane 
• 89543-87-3 1-(3-phenyl-isoxazolin-5-yl)ethane-1,2-diol 
• 119496-37-6 (tert-Butyl-dimethyl-silanyloxy)-(3-phenyl-4,5-dihydro-isoxazol-5-yl)-acetaldehyde 
• 119496-13-8 5-[1-(tert-Butyl-dimethyl-silanyloxy)-2,2-bis-tert-butylsulfanyl-ethyl]-3-phenyl-4,5-dihydro-isoxazole 
• 67-64-1 acetone 

Downstream Products

• 93106-31-1 ribo-5-amino-5-phenyl-1,2,3-pentanetriol 1,2-acetonide 
• 93106-31-1 arabino-5-amino-5-phenyl-1,2,3-pentanetriol 1,2-acetonide 
• 93106-31-1 (1S,3S)-3-Amino-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-phenyl-propan-1-ol 
• 93106-31-1 (1S,3R)-3-Amino-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-phenyl-propan-1-ol 

Relevant academic research and scientific papers

1,3-dipolar cycloaddition of chirally modified vinylboronic ester with nitrile oxides

Chiral modified vinylboronic ester 1, derived from D-(+)-mannitol, reacted with nitrile oxides to afford optically active isoxazolines. The regioselectivity was excellent and moderate stereoselectivity (up to 60% d.e.) was achieved. The configuration of new chiral centres in all the isoxazoline products was established by NMR analysis or X-ray analysis. (C) 2000 Elsevier Science Ltd.

DIASTEREOSELECTIVE NITRILE OXIDE CYCLOADDITIONS TO CHIRAL ALLYL ETHERS DERIVED FROM 1,1-DITHIO-3-BUTEN-2-OLS.

Highly diastereoselective cycloaddition of nitrile oxides to the title compounds gives masked polyfunctional products amenable to a variety of synthetic elaboration; an entry to enantiomerically pure derivatives is described.

Stereoselective Osmylation of 5-Vinyl-4,5-dihydroisoxazoles

Osmium tetroxide-catalysed cis-hydroxylation of 5-vinyl-4,5-dihydroisoxazoles proceeds stereoselectively affording the anti-products in fair to excellent diastereoisomeric excess; an entry to optically active compounds is also described.

Stereoselective Synthesis of Masked Amino-polyols via Osmylation of 4,5-Dihydro-5-vinylisoxazoles

Variously substituted 4,5-dihydro-5-vinylisoxazoles, obtained by regio- and stereospecific cycloaddition of nitrile oxides to dienes, undergo smooth OsO4-catalyzed cis-hydroxylation to give amino-polyol precursors.The reaction is 'anti'-selective, the dia

Diastereofacial Selection in Nitrile Oxide Cycloaddition Reactions. The Anti-Directing Effect of an Allylic Oxygen and Some New Results on the Ring Metalation of Isoxazolines. A Synthesis of (+/-)-Blastmycinone

The extent of diastereoselectivity associated with the reactions of nitrile oxides with alkenes bearing an allylic oxygen substituent has been studied.Reasonable levels of such diastereoselectivity have been found when the tert-butyldimethylsilyl ether derivative of 3-buten-2-ol (5) or (+)-(S)-isopropylidene-3-butene-1,2-diol (1) are employed as dipolarophiles.The stereochemical course of these cycloaddition reactions has been proven rigorously through the transformation of the adducts to known γ-lactones.The stereochemistry associated with the metalation/alkylation of 5-alkoxymethyl-substituted isoxazolines has also been probed in order to further expand the use of these heterocycles as aldol equivalents in natural products total synthesis.A synthesis of (+/-)-blastmycinone (34) is reported which combines the two foregoing aspects of stereocontrol.The levels of regio- and stereoselectivity found in the cycloaddition reactions of the cis- and trans-disubstituted alkenes 35 and 39 prepared from isopropylidene-D-glyceraldehyde are also discussed.A single example of the reaction of a chiral alkene with a chiral nitrile is presented.

SYNTHESIS OF AMINO SUGARS VIA ISOXAZOLINES. DL- AND D-LIVIDOSAMINE (2-AMINO-2,3-DIDEOXY-RIBO-HEXOSE) DERIVATIVES FROM 4-VINYL-1,3-DIOXOLANES AND NITROACETALDEHYDE ACETALS

1,3-Dipolar cycloaddition of nitrile oxides, generated from nitroethanol and nitroacetaldehyde derivatives 3, 21 and 22, respectively, and of benzonitrile oxide to 4-vinyldioxolanes 1,2 gave ca 4:1 erythro/threo mixtures of corresponding isoxazolines.LAH reduction of erytho isoxazolines proceeded with similar (ca4:1) selectivity to furnish protected ribo-amino-polyols 11, 15, 19, DL- and D-lividosamines 31 and 33, respectively, as main products.The DL-lividosamine derivative 33 was obtained pure by crystallization.In the D-series, the corresponding ribo/arabino mixture D-31/D-32 was transformed to the known α-methyl D-lividosaminide D-37.