FRINK Linked Data Fragments server

Matches in SemOpenAlex for { <https://semopenalex.org/work/W2028163901> ?p ?o ?g. }

• W2028163901 endingPage "1706" @default.
• W2028163901 startingPage "1702" @default.
• W2028163901 abstract "The samarium(II) iodide mediated asymmetric Reformatsky-type reaction of chiral 3-bromoacetyl-2-oxazolidinones with various aldehydes was studied. A series of chiral 4-substituted 2-oxazolidinones 1-3 and 5,5-disubstituted SuperQuat oxazolidinones 4-5 were employed as chiral auxiliaries of the alpha-bromoacetic acid. The reaction of 1 with various aldehydes gave the alpha-unbranched beta-hydroxy carboximides in good yields with high diastereomeric excess values (up to >99% de). The majority of the reaction product derived from 5,5-diphenyl SuperQuat 5 were highly crystallinity; a single recrystallization yielding a diastereomerically pure product with the other diastereomer not detectable by spectroscopic methods. The absolute configurations of the beta-hydroxy carboximides were determined by signs of optical rotations of the corresponding known ethyl esters referring to the literature values. Hydrolytic cleavage of the appended of beta-hydroxy moieties from the auxiliary SuperQuats was readily achieved under mild conditions using lithium hydroxide; the corresponding carboxylic acids and the returned SuperQuats were obtained in good yields without any evidence of racemization. The first step of the reaction is the reduction of the alpha-bromo group to produce the samarium enolate, which adds to an aldehyde. The absolute configuration of the adduct (7i) derive from benzaldehyde was found to be R, with the samarium enolate favoring the transition state predicted from chelation control of the reagent; this is in analogy to the discussion that has been used for the corresponding titanium enolate. The stereochemistry of the reaction may be explained by incorporating the Nerz-Stormes-Thornton chair transition structure model." @default.
• W2028163901 created "2016-06-24" @default.
• W2028163901 creator A5037982236 @default.
• W2028163901 creator A5083428701 @default.
• W2028163901 creator A5090867811 @default.
• W2028163901 date "2000-02-19" @default.
• W2028163901 modified "2023-10-02" @default.
• W2028163901 title "Asymmetric Samarium-Reformatsky Reaction of Chiral α-Bromoacetyl-2-oxazolidinones with Aldehydes" @default.
• W2028163901 cites W1968436252 @default.
• W2028163901 cites W1968498689 @default.
• W2028163901 cites W1972295774 @default.
• W2028163901 cites W1972316551 @default.
• W2028163901 cites W2009884860 @default.
• W2028163901 cites W2050742563 @default.
• W2028163901 cites W2056421367 @default.
• W2028163901 cites W2070673326 @default.
• W2028163901 cites W2128949728 @default.
• W2028163901 cites W2136109670 @default.
• W2028163901 cites W2158769459 @default.
• W2028163901 cites W2949225583 @default.
• W2028163901 cites W2949262770 @default.
• W2028163901 cites W2949487620 @default.
• W2028163901 cites W2950298679 @default.
• W2028163901 cites W2950982239 @default.
• W2028163901 cites W2951137913 @default.
• W2028163901 cites W2951527830 @default.
• W2028163901 cites W2952578031 @default.
• W2028163901 cites W2952639395 @default.
• W2028163901 cites W2953359365 @default.
• W2028163901 cites W3042443450 @default.
• W2028163901 cites W3198356047 @default.
• W2028163901 cites W4252331710 @default.
• W2028163901 doi "https://doi.org/10.1021/jo9914317" @default.
• W2028163901 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/10814143" @default.
• W2028163901 hasPublicationYear "2000" @default.
• W2028163901 type Work @default.
• W2028163901 sameAs 2028163901 @default.
• W2028163901 citedByCount "98" @default.
• W2028163901 countsByYear W20281639012012 @default.
• W2028163901 countsByYear W20281639012013 @default.
• W2028163901 countsByYear W20281639012014 @default.
• W2028163901 countsByYear W20281639012015 @default.
• W2028163901 countsByYear W20281639012016 @default.
• W2028163901 countsByYear W20281639012017 @default.
• W2028163901 countsByYear W20281639012018 @default.
• W2028163901 countsByYear W20281639012019 @default.
• W2028163901 countsByYear W20281639012020 @default.
• W2028163901 countsByYear W20281639012021 @default.
• W2028163901 countsByYear W20281639012022 @default.
• W2028163901 countsByYear W20281639012023 @default.
• W2028163901 crossrefType "journal-article" @default.
• W2028163901 hasAuthorship W2028163901A5037982236 @default.
• W2028163901 hasAuthorship W2028163901A5083428701 @default.
• W2028163901 hasAuthorship W2028163901A5090867811 @default.
• W2028163901 hasConcept C138716334 @default.
• W2028163901 hasConcept C146686406 @default.
• W2028163901 hasConcept C155647269 @default.
• W2028163901 hasConcept C161790260 @default.
• W2028163901 hasConcept C178790620 @default.
• W2028163901 hasConcept C185592680 @default.
• W2028163901 hasConcept C25170562 @default.
• W2028163901 hasConcept C2777738585 @default.
• W2028163901 hasConcept C2778886288 @default.
• W2028163901 hasConcept C2779061078 @default.
• W2028163901 hasConcept C2779692420 @default.
• W2028163901 hasConcept C2779825165 @default.
• W2028163901 hasConcept C3141732 @default.
• W2028163901 hasConcept C40875361 @default.
• W2028163901 hasConcept C536819264 @default.
• W2028163901 hasConcept C60002323 @default.
• W2028163901 hasConcept C71240020 @default.
• W2028163901 hasConceptScore W2028163901C138716334 @default.
• W2028163901 hasConceptScore W2028163901C146686406 @default.
• W2028163901 hasConceptScore W2028163901C155647269 @default.
• W2028163901 hasConceptScore W2028163901C161790260 @default.
• W2028163901 hasConceptScore W2028163901C178790620 @default.
• W2028163901 hasConceptScore W2028163901C185592680 @default.
• W2028163901 hasConceptScore W2028163901C25170562 @default.
• W2028163901 hasConceptScore W2028163901C2777738585 @default.
• W2028163901 hasConceptScore W2028163901C2778886288 @default.
• W2028163901 hasConceptScore W2028163901C2779061078 @default.
• W2028163901 hasConceptScore W2028163901C2779692420 @default.
• W2028163901 hasConceptScore W2028163901C2779825165 @default.
• W2028163901 hasConceptScore W2028163901C3141732 @default.
• W2028163901 hasConceptScore W2028163901C40875361 @default.
• W2028163901 hasConceptScore W2028163901C536819264 @default.
• W2028163901 hasConceptScore W2028163901C60002323 @default.
• W2028163901 hasConceptScore W2028163901C71240020 @default.
• W2028163901 hasIssue "6" @default.
• W2028163901 hasLocation W20281639011 @default.
• W2028163901 hasLocation W20281639012 @default.
• W2028163901 hasOpenAccess W2028163901 @default.
• W2028163901 hasPrimaryLocation W20281639011 @default.
• W2028163901 hasRelatedWork W1995436685 @default.
• W2028163901 hasRelatedWork W2028163901 @default.
• W2028163901 hasRelatedWork W2031503377 @default.
• W2028163901 hasRelatedWork W2094700735 @default.
• W2028163901 hasRelatedWork W2146152657 @default.

• next