17669-24-8

Upstream product

• 873-67-6 benzonitrile oxide 
• 624-64-6 trans-2-Butene 
• 17669-23-7 3-phenyl-cis-4,5-dimethyl-Δ²-isoxazoline 
• 698-16-8 benzohydroximoyl chloride 

Downstream Products

• 42563-57-5 β-(2R,3S,4R)/(2S,3R,4S)-4-Amino-3-methyl-4-phenyl-2-butanol 
• 42563-57-5 α-(2R,3S,4S)/(2S,3R,4R)-4-Amino-3-methyl-4-phenyl-2-butanol 
• 86542-09-8 (2RS,3RS)-3-hydroxy-2-methyl-1-phenylbutan-1-one 

Relevant academic research and scientific papers

REDUCTION OF DELTA 2-ISOXAZOLINES. PART 3: RANEY-NICKEL CATALYZED FORMATION OF beta -HYDROXY KETONES.

The importance of the beta -hydroxy ketone moiety has led to the development of a wide variety of aldol type methodologies for its construction. A conceptually new approach to these 'aldol adducts' is presented on the basis of left bracket 3 plus 2 right bracket dipolar cycloaddition of in situ generated nitrile oxides and olefins followed by reduction of the resulting DELTA **2-isoxazolines. This approach provides a nice complement of the aldol type reaction. Optimum conditions for the transformation of DELTA **2-isoxazolines to beta -hydroxy ketones use Raney-nickel catalyst, boric acid, 5/1 MeOH/H//2O, and hydrogen gas. Under these mild conditions, 3-methyl-5-n-butyl- DELTA **2-isoxazoline is transformed to 4-hydroxy-2-octanone in high yield. Thus 'directed aldol' type adducts are readily available by selection of the appropriate olefin and nitrile oxide precursor (usually the 1 degree nitro compound).

Syntheses via Isoxazolines, 6. - Asymmetric Induction in the Reduction of 2-Isoxazolines to Yield γ-Amino Alcohols with Two or Three Vicinal Stereocentres

The substituted 3-aminopropanols 3 and 5 with two or three adjacent chiral centres are prepared from alkenes and nitrile oxides via LiAlH4 reduction of intermediate isoxazolines 2 and 4, respectively, in a regio- and stereoselective mode. 4-Alkyl groups g