1992
DOI: 10.1016/0008-6215(92)84181-q
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Cycloaddition of nitrile oxides to 3- O -benzyl-5,6-dideoxy-1,2- O -isopropylidene-α- d - ribo -hex-5-enofuranose

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Cited by 10 publications
(2 citation statements)
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“…The major diastereomers of the adducts 136 have the R-configurations of the newly formed chiral centres. Quite a different result is obtained for the corresponding D-ribose derivative 135c, 113,115 which represents an epimer of compound 135a as regards the homoallylic C(3) atom. In this case, the syn-and anti-adducts 136 and 137 are formed in approximately equal amounts.…”
Section: The Nitrile Oxide Methods In Carbohydrate Chemistrymentioning
confidence: 93%
“…The major diastereomers of the adducts 136 have the R-configurations of the newly formed chiral centres. Quite a different result is obtained for the corresponding D-ribose derivative 135c, 113,115 which represents an epimer of compound 135a as regards the homoallylic C(3) atom. In this case, the syn-and anti-adducts 136 and 137 are formed in approximately equal amounts.…”
Section: The Nitrile Oxide Methods In Carbohydrate Chemistrymentioning
confidence: 93%
“…11 It is worth noting that generally 1,3-DCA of (1) with substrates of type (4) takes place with lower selectivity than the corresponding Diels-Alder reactions, 11,12 and Lewis acids retard the 1,3-DCA and decrease yields with no improvement in diastereoselectivity. Higher diastereoselectivity (80-90% de) is observed if bornyl crotonates, 13 chiral imides, 14 alkenes containing a chiral imidazolidine controller, 15 or carbohydrates 16 Acryloylsultams such as (5) 17a and (S)-and (R)-(6) 17b are the best auxiliaries for almost complete asymmetric induction yielding, after reduction, enantiomerically pure isoxazolines (eq 7). Because the 2 -isoxazoline ring can be readily cleaved, this chemistry provides a powerful approach to the synthesis of polyfunctional compounds from alkenes.…”
Section: O Hsmentioning
confidence: 99%