Matches in SemOpenAlex for { <https://semopenalex.org/work/W3089531415> ?p ?o ?g. }
- W3089531415 endingPage "8121" @default.
- W3089531415 startingPage "8116" @default.
- W3089531415 abstract "The development of an asymmetric “clip-cycle” synthesis of 2,2- and 3,3-disubstituted pyrrolidines and spiropyrrolidines, which are increasingly important scaffolds in drug discovery programs, is reported. Cbz-protected bis-homoallylic amines were activated by “clipping” them to thioacrylate via an alkene metathesis reaction. Enantioselective intramolecular aza-Michael cyclization onto the activated alkene, catalyzed by a chiral phosphoric acid, formed a pyrrolidine. The reaction accommodated a range of substitutions to form 2,2- and 3,3-disubstituted pyrrolidines and spiropyrrolidines with high enantioselectivities. The importance of the thioester activating group was demonstrated by comparison to ketone and oxoester-containing substrates. DFT studies supported the aza-Michael cyclization as the rate- and stereochemistry-determining step and correctly predicted the formation of the major enantiomer. The catalytic asymmetric syntheses of N-methylpyrrolidine alkaloids (R)-irnidine and (R)-bgugaine, which possess DNA binding and antibacterial properties, were achieved using the “clip-cycle” methodology." @default.
- W3089531415 created "2020-10-08" @default.
- W3089531415 creator A5037081452 @default.
- W3089531415 creator A5063312579 @default.
- W3089531415 creator A5090365494 @default.
- W3089531415 date "2020-09-29" @default.
- W3089531415 modified "2023-10-14" @default.
- W3089531415 title "Asymmetric “Clip-Cycle” Synthesis of Pyrrolidines and Spiropyrrolidines" @default.
- W3089531415 cites W1867552515 @default.
- W3089531415 cites W1966098686 @default.
- W3089531415 cites W1968349194 @default.
- W3089531415 cites W1979968827 @default.
- W3089531415 cites W1981374319 @default.
- W3089531415 cites W1981809563 @default.
- W3089531415 cites W1988091937 @default.
- W3089531415 cites W2000079595 @default.
- W3089531415 cites W2003155487 @default.
- W3089531415 cites W2003583336 @default.
- W3089531415 cites W2011215428 @default.
- W3089531415 cites W2021226908 @default.
- W3089531415 cites W2023271753 @default.
- W3089531415 cites W2023860486 @default.
- W3089531415 cites W2029526231 @default.
- W3089531415 cites W2030560333 @default.
- W3089531415 cites W2034473501 @default.
- W3089531415 cites W2040333979 @default.
- W3089531415 cites W2041703891 @default.
- W3089531415 cites W2046412723 @default.
- W3089531415 cites W2066175756 @default.
- W3089531415 cites W2070411055 @default.
- W3089531415 cites W2083134342 @default.
- W3089531415 cites W2086957099 @default.
- W3089531415 cites W2094642658 @default.
- W3089531415 cites W2119547517 @default.
- W3089531415 cites W2123374252 @default.
- W3089531415 cites W2123774442 @default.
- W3089531415 cites W2135986133 @default.
- W3089531415 cites W2143981217 @default.
- W3089531415 cites W2148514342 @default.
- W3089531415 cites W2149052823 @default.
- W3089531415 cites W2150697053 @default.
- W3089531415 cites W2152121631 @default.
- W3089531415 cites W2159415955 @default.
- W3089531415 cites W2329235087 @default.
- W3089531415 cites W2401558437 @default.
- W3089531415 cites W2407040666 @default.
- W3089531415 cites W2516019540 @default.
- W3089531415 cites W2552667341 @default.
- W3089531415 cites W2617283258 @default.
- W3089531415 cites W2734795396 @default.
- W3089531415 cites W2758915380 @default.
- W3089531415 cites W2793280121 @default.
- W3089531415 cites W2795155247 @default.
- W3089531415 cites W2886082479 @default.
- W3089531415 cites W2911511582 @default.
- W3089531415 cites W2912521389 @default.
- W3089531415 cites W2926202212 @default.
- W3089531415 cites W2944203732 @default.
- W3089531415 cites W2947230025 @default.
- W3089531415 cites W2949922114 @default.
- W3089531415 cites W2950241036 @default.
- W3089531415 cites W2950795628 @default.
- W3089531415 cites W2950976533 @default.
- W3089531415 cites W2950998926 @default.
- W3089531415 cites W2952077728 @default.
- W3089531415 cites W2953169775 @default.
- W3089531415 cites W2965331257 @default.
- W3089531415 cites W2978631752 @default.
- W3089531415 cites W3008636619 @default.
- W3089531415 doi "https://doi.org/10.1021/acs.orglett.0c03090" @default.
- W3089531415 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/32991808" @default.
- W3089531415 hasPublicationYear "2020" @default.
- W3089531415 type Work @default.
- W3089531415 sameAs 3089531415 @default.
- W3089531415 citedByCount "15" @default.
- W3089531415 countsByYear W30895314152021 @default.
- W3089531415 countsByYear W30895314152022 @default.
- W3089531415 countsByYear W30895314152023 @default.
- W3089531415 crossrefType "journal-article" @default.
- W3089531415 hasAuthorship W3089531415A5037081452 @default.
- W3089531415 hasAuthorship W3089531415A5063312579 @default.
- W3089531415 hasAuthorship W3089531415A5090365494 @default.
- W3089531415 hasBestOaLocation W30895314152 @default.
- W3089531415 hasConcept C112423150 @default.
- W3089531415 hasConcept C146686406 @default.
- W3089531415 hasConcept C161790260 @default.
- W3089531415 hasConcept C178790620 @default.
- W3089531415 hasConcept C185592680 @default.
- W3089531415 hasConcept C21951064 @default.
- W3089531415 hasConcept C2776254738 @default.
- W3089531415 hasConcept C2777738585 @default.
- W3089531415 hasConcept C2778851528 @default.
- W3089531415 hasConcept C63338738 @default.
- W3089531415 hasConcept C71240020 @default.
- W3089531415 hasConcept C75079739 @default.
- W3089531415 hasConceptScore W3089531415C112423150 @default.
- W3089531415 hasConceptScore W3089531415C146686406 @default.
- W3089531415 hasConceptScore W3089531415C161790260 @default.