Journal of the American Chemical Society p. 5826 - 5833 (1983)
Update date:2022-08-03
Curran
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).
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Doi:10.1021/jm00349a024
(1982)Doi:10.1021/jm00350a009
(1982)Doi:10.1002/ejic.200400130
(2004)Doi:10.1007/s11746-009-1471-7
(2010)Doi:10.1002/ejic.200400083
(2004)Doi:10.1248/cpb.30.3160
(1982)