Ni-catalyzed homoallylation of polyhydroxy N,O- Acetals with conjugated dienes promoted by triethylborane
In the presence of Ni-catalyst and triethylborane, N,O- Acetals prepared from glycolaldehyde and glyceraldehyde with primary amines in situ underwent homoallylation with conjugated dienes to provide 2- Amino-5-hexenols in high regio- And stereoselectivity
Chemistry of O-Silylated Ketene Acetals: Stereocontrolled Synthesis of 2-Deoxy- and 2-Deoxy-2-C-alkyl-erythro-pentoses
Diastereoselective aldol reactions of 2,3-O-isopropylidene-D-(and L-)-glyceraldehydes (D- and L-2) with ketene silyl acetal 1a occurred in acetonitrile under mild conditions to give the corresponding anti-β-siloxy esters (D- and L-3a) as major products, which were converted to 2-deoxy-D-(and L-) riboses through a few additional steps.The aldol reactions of D-2 with α-monoalkyl-substituted ketene silyl acetals 1c-f proceeded similarly to give all anti-α-alkyl-β-siloxy esters (11a-14a) as major products, which were converted into 2-deoxy-2-C-alkyl-erythro-pentoses (17a,b).
THE CHEMISTRY OF O-SILYLATED KETENE ACETALS; DIASTEREOSELECTIVE ALDOL REACTION OF 2,3-O-ISOPROPYLIDENE-D (AND L)-GLYCERALDEHYDES LEADING TO 2-DEOXY-D (AND L)-RIBOSES
Diastereoselective carbon-carbon bond forming reaction of 2,3-O-isopropylidene-D (and L)-glyceraldehydes (D and L-2) with ketene silyl acetals (1a,b) occured in acetonitrile under mild conditions to give the corresponding anti-β-siloxyesters (D and L-3a) as major products, which could be converted through a few additional steps to 2-deoxy-D (and L)-riboses.
Kita, Yasuyuki,Yasuda, Hitoshi,Tamura, Osamu,Itoh, Fumio,Ke, Ya Yuan,Tamura, Yasumitsu
p. 5777 - 5780
(2007/10/02)
A NEW METHOD FOR THE GENERATION OF A BORON ENOLATE OF AN ESTER - A NEW SYNTHESIS OF 2-DEOXY-D-RIBOSE -
A boron enolate of an ester was generated in situ by the treatment of ethoxyacetylene with mercury(II) acetate and diphenylborinic acid, and the boron enolate thus formed further reacted with aldehydes to give β-hydroxyesters and β-acetoxyesters in good yields.The reaction was successfully applied to the stereoselective synthesis of 2-deoxy-D-ribose.
Murakami, Masahiro,Mukaiyama, Teruaki
p. 241 - 244
(2007/10/02)
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