Matches in SemOpenAlex for { <https://semopenalex.org/work/W3021570698> ?p ?o ?g. }
- W3021570698 endingPage "9180" @default.
- W3021570698 startingPage "9175" @default.
- W3021570698 abstract "A precisely designed chiral squaramide derivative is shown to promote the highly enantioselective addition of trimethylsilyl bromide (TMSBr) to a broad variety of 3-substituted and 3,3-disubstituted oxetanes. The reaction provides direct and general access to synthetically valuable 1,3-bromohydrin building blocks from easily accessed achiral precursors. The products are readily elaborated both by nucleophilic substitution and through transition-metal-catalyzed cross-coupling reactions. The enantioselective catalytic oxetane ring opening was employed as part of a three-step, gram-scale synthesis of pretomanid, a recently approved medication for the treatment of multidrug-resistant tuberculosis. Heavy-atom kinetic isotope effect (KIE) studies are consistent with enantiodetermining delivery of bromide from the H-bond-donor (HBD) catalyst to the activated oxetane. While the nucleophilicity of the bromide ion is expected to be attenuated by association to the HBD, overall rate acceleration is achieved by enhancement of Lewis acidity of the TMSBr reagent through anion abstraction." @default.
- W3021570698 created "2020-05-13" @default.
- W3021570698 creator A5031428200 @default.
- W3021570698 creator A5034934833 @default.
- W3021570698 creator A5037736695 @default.
- W3021570698 creator A5044150277 @default.
- W3021570698 date "2020-05-04" @default.
- W3021570698 modified "2023-10-03" @default.
- W3021570698 title "Highly Enantioselective, Hydrogen-Bond-Donor Catalyzed Additions to Oxetanes" @default.
- W3021570698 cites W1593167595 @default.
- W3021570698 cites W1963591519 @default.
- W3021570698 cites W1964297120 @default.
- W3021570698 cites W1965449936 @default.
- W3021570698 cites W1966937884 @default.
- W3021570698 cites W1973003325 @default.
- W3021570698 cites W1974797520 @default.
- W3021570698 cites W1975346398 @default.
- W3021570698 cites W1976947722 @default.
- W3021570698 cites W1978851116 @default.
- W3021570698 cites W1979259658 @default.
- W3021570698 cites W1984926282 @default.
- W3021570698 cites W1998049497 @default.
- W3021570698 cites W2001805649 @default.
- W3021570698 cites W2003125534 @default.
- W3021570698 cites W2003870591 @default.
- W3021570698 cites W2034475135 @default.
- W3021570698 cites W2035431420 @default.
- W3021570698 cites W2042650350 @default.
- W3021570698 cites W2045371205 @default.
- W3021570698 cites W2049807720 @default.
- W3021570698 cites W2060863510 @default.
- W3021570698 cites W2060968428 @default.
- W3021570698 cites W2061395384 @default.
- W3021570698 cites W2062590568 @default.
- W3021570698 cites W2064216426 @default.
- W3021570698 cites W2064815026 @default.
- W3021570698 cites W2071508592 @default.
- W3021570698 cites W2071801044 @default.
- W3021570698 cites W2076411479 @default.
- W3021570698 cites W2079561045 @default.
- W3021570698 cites W2085196370 @default.
- W3021570698 cites W2085243851 @default.
- W3021570698 cites W2085351645 @default.
- W3021570698 cites W2090291993 @default.
- W3021570698 cites W2092540550 @default.
- W3021570698 cites W2103729102 @default.
- W3021570698 cites W2114466724 @default.
- W3021570698 cites W2132515598 @default.
- W3021570698 cites W2143729242 @default.
- W3021570698 cites W2158974750 @default.
- W3021570698 cites W2164181867 @default.
- W3021570698 cites W2216567860 @default.
- W3021570698 cites W2327675919 @default.
- W3021570698 cites W2333617155 @default.
- W3021570698 cites W2343118341 @default.
- W3021570698 cites W2463435724 @default.
- W3021570698 cites W2519006730 @default.
- W3021570698 cites W2582121544 @default.
- W3021570698 cites W2767817928 @default.
- W3021570698 cites W2787880525 @default.
- W3021570698 cites W2799471671 @default.
- W3021570698 cites W2801715076 @default.
- W3021570698 cites W2911570773 @default.
- W3021570698 cites W2926146520 @default.
- W3021570698 cites W2949752723 @default.
- W3021570698 cites W2950297465 @default.
- W3021570698 cites W2950705309 @default.
- W3021570698 cites W2952138580 @default.
- W3021570698 cites W2952315273 @default.
- W3021570698 cites W2975491171 @default.
- W3021570698 cites W4254697392 @default.
- W3021570698 cites W4367435825 @default.
- W3021570698 cites W86697786 @default.
- W3021570698 doi "https://doi.org/10.1021/jacs.0c03991" @default.
- W3021570698 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/7293824" @default.
- W3021570698 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/32364378" @default.
- W3021570698 hasPublicationYear "2020" @default.
- W3021570698 type Work @default.
- W3021570698 sameAs 3021570698 @default.
- W3021570698 citedByCount "41" @default.
- W3021570698 countsByYear W30215706982020 @default.
- W3021570698 countsByYear W30215706982021 @default.
- W3021570698 countsByYear W30215706982022 @default.
- W3021570698 countsByYear W30215706982023 @default.
- W3021570698 crossrefType "journal-article" @default.
- W3021570698 hasAuthorship W3021570698A5031428200 @default.
- W3021570698 hasAuthorship W3021570698A5034934833 @default.
- W3021570698 hasAuthorship W3021570698A5037736695 @default.
- W3021570698 hasAuthorship W3021570698A5044150277 @default.
- W3021570698 hasBestOaLocation W30215706982 @default.
- W3021570698 hasConcept C121332964 @default.
- W3021570698 hasConcept C135731615 @default.
- W3021570698 hasConcept C146686406 @default.
- W3021570698 hasConcept C155647269 @default.
- W3021570698 hasConcept C161790260 @default.
- W3021570698 hasConcept C178790620 @default.
- W3021570698 hasConcept C178907741 @default.
- W3021570698 hasConcept C185592680 @default.