1999
DOI: 10.1021/jo991227j
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1,3-Dipolar Cycloadditions of Diazomethane to Chiral Electron-Deficient Olefins:  The Origin of the π-Facial Diastereoselection

Abstract: The stereochemical outcome of diazomethane cycloadditions to several chiral electron-deficient olefins has been investigated in order to establish the origin of the pi-facial diastereoselection. Nitro olefins, vinyl sulfones, enoates, and 2-amino enoates have been used for such a purpose. These substrates have been prepared from D-glyceraldehyde acetonide through Wittig-type condensations and present an alkoxy substituent, provided by the bulky dioxolane ring, attached to the stereogenic allylic carbon. Syn-ad… Show more

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Cited by 38 publications
(19 citation statements)
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“…This result is in accordance with the stereochemical outcome of the addition of diazomethane 19 and diazo compound 1 15 to chiral olefins derived from aldehyde 4, which were previously investigated in our laboratory.…”
Section: Reaction Of Carbene 2 With Aldehydesupporting
confidence: 90%
“…This result is in accordance with the stereochemical outcome of the addition of diazomethane 19 and diazo compound 1 15 to chiral olefins derived from aldehyde 4, which were previously investigated in our laboratory.…”
Section: Reaction Of Carbene 2 With Aldehydesupporting
confidence: 90%
“…It was the heterocycle 5,8-dihydroxy-1H-benzo[f]indazole -4,9dion (29), which had evidently been formed by a [1,3]-dipolar cycloaddition ([3 ? 2]-cycloaddition of diazomethane (Houk and Luskus 1970;Muray et al 2000)) to the quinoid C2-C3-double bond in DHNQ, followed by oxidation of the primary intermediate 28.…”
Section: Attempted Methylation Of Dhnq With Diazomethanementioning
confidence: 99%
“…Studies of diastereoselective 1,3-dipolar cycloadditions with alkenes 71-75 and related derivatives of chiral allyl alcohols are a good example for this variability with respect to the stereochemical outcome of these reactions. 70 Substrates 71-75 ( Figure 6) have been used extensively for 1,3-dipolar cycloadditions with diazoalkanes to give syn-and anti-pyrazolines 76-80 (dependent upon alkene geometry) with high diastereoselectivity (Table 7). It is interesting to note that anti-configured cycloaddition products predominate if chiral allyl amines are used as educts.…”
Section: Figurementioning
confidence: 99%