Determination of the Absolute Configuration of 3-Pyrrolin-2-ones

Cuiper, Agnes D.; Brzostowska, Małgorzata; Gawroński, Jacek; Smeets, Wilberth J. J.; Spek, Anthony L.; Hiemstra, Henk; Kellogg, Richard M.; Feringa, Ben L.

doi:10.1021/jo982151e

Cited by 26 publications

(10 citation statements)

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“…47 Gotor's group assigned the absolute configuration of pyridyl alcohols by a combination of the sign of optical rotation, elution order in HPLC and the emprical rule for lipase-catalyzed resolutions (Entry 7). The derivatives where R 5 Me or Et have established absolute configurations and served as the reference compounds.…”

Section: Examplesmentioning

confidence: 99%

Determination of absolute configuration of secondary alcohols using lipase‐catalyzed kinetic resolutions

Jing

Kazlauskas

2008

Chirality

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Lipases show high enantioselectivity toward a wide range of secondary alcohols. An empirical rule based on the relative sizes of the substituents predicts which enantiomer reacts faster. X-ray structures of lipases provide a molecular basis for this empirical rule: their alcohol-binding pocket contains large hydrophobic pocket open to solvent and another smaller pocket. This predictable enantiopreference of lipases allows the determination of the absolute configuration of secondary alcohols using lipase-catalyzed kinetic resolution. Researchers have used this relative method to determine the configuration of approximately 50 secondary alcohols either as the only method or in combination with other methods.

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Section: Examplesmentioning

confidence: 99%

Determination of absolute configuration of secondary alcohols using lipase‐catalyzed kinetic resolutions

Jing

Kazlauskas

2008

Chirality

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“…The characteristic features for each pair of enantiomers were summarized in Table 3 . The empirical CD rules have been successfully employed in determining the stereochemistry of the α , β -unsaturated lactone or lactam rings in various natural products 27 28 29 . However, it seems that the rules are not entirely applicable to these four pairs of germacrane-type sesquiterpenes, which could be attributed to the neighboring high conformational flexible ten-membered ring and the presence of the polyunsaturated conjugated chromophores around the stereogenic center (C-8) 28 29 .…”

Section: Discussionmentioning

confidence: 99%

(+)/(−)-Phaeocaulin A-D, four pairs of new enantiomeric germacrane-type sesquiterpenes from Curcuma phaeocaulis as natural nitric oxide inhibitors

Xia

Sun

et al. 2017

Sci Rep

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Germacrane-type sesquiterpenes, with a flexible 10-membered ring unit as the structural and conformational features, play a central role in the biosynthesis and synthesis of other sesquiterpenes. In this report, two pairs of new sesquiterpene alkaloids, (+)/(−)-phaeocaulin A [(+)-1/(−)-1] and B [(+)-2/(−)-2], and two pairs of new sesquiterpenes, (+)/(−)-phaeocaulin C [(+)-3/(−)-3] and D [(+)-4/(−)-4], along with one related known analog (5), were isolated from the rhizomes of Curcuma phaeocaulis. The absolute configurations of (+)-1/(−)-1, (+)-2/(−)-2, (+)-3/(−)-3 and (+)-4/(−)-4 were unambiguously determined by analysis of single-crystal X-ray diffractions and quantum chemical electronic circular dichroism (ECD) method. It is noteworthy that (+)/(−)-phaeocaulin A [(+)-1/(−)-1] and B [(+)-2/(−)-2] are two pairs of rare N-containing germacrane-type sesquiterpenes. A possible biogenetic pathway for 1–5 was postulated. All of the isolated compounds were tested for their inhibitory activity against LPS-induced nitric oxide production in RAW 264.7 macrophages.

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“…Racemic 5-acetoxy-1-acetyl-3-pyrrolin-2-one, (I), was synthesized in two steps starting from methoxyfuranone (van der Deen et al, 1996). Both enantiomers of this synthon can be enantiomerically purified in high yield by a chemo-enzymatic route (van der Deen et al, 1996) and the absolute configuration can be determined by circular dichroism measurements or from the crystal structure of the corresponding tetracarbonyl iron complex (Cuiper et al, 1999). This acyloxypyrrolinone can, for example, be converted into the N-acyliminium precursor 5-isopropoxypyrrolinone (Goubitz et al, 1996) with retention of configuration by means of a palladium-catalyzed allylic substitution (Cuiper et al, 1998).…”

Section: Commentmentioning

confidence: 99%

5-Acetoxy-1-acetyl-3-pyrrolin-2-one

2005

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Determination of the Absolute Configuration of 3-Pyrrolin-2-ones

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Cited by 26 publications

References 29 publications

Determination of absolute configuration of secondary alcohols using lipase‐catalyzed kinetic resolutions

Determination of absolute configuration of secondary alcohols using lipase‐catalyzed kinetic resolutions

(+)/(−)-Phaeocaulin A-D, four pairs of new enantiomeric germacrane-type sesquiterpenes from Curcuma phaeocaulis as natural nitric oxide inhibitors

5-Acetoxy-1-acetyl-3-pyrrolin-2-one

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