Lovering, F., Bikker, J. & Humblet, C. Escape from flatland: increasing saturation as an approach to improving clinical success. J. Med. Chem. 52, 6752–6756 (2009).
Article CAS PubMed Google Scholar
Zhuo, C.-X., Zhang, W. & You, S.-L. Catalytic asymmetric dearomatization reactions. Angew. Chem. Int. Ed. 51, 12662–12686 (2012).
Zheng, C. & You, S.-L. Catalytic asymmetric dearomatization by transition-metal catalysis: a method for transformations of aromatic compounds. Chem 1, 830–857 (2016).
Wertjes, W. C., Southgate, E. H. & Sarlah, D. Recent advances in chemical dearomatization of nonactivated arenes. Chem. Soc. Rev. 47, 7996–8017 (2018).
Article CAS PubMed Google Scholar
Huck, C. J. & Sarlah, D. Shaping molecular landscapes: recent advances, opportunities, and challenges in dearomatization. Chem 6, 1589–1603 (2020).
Article CAS PubMed PubMed Central Google Scholar
Zhuo, C.-X., Zheng, C. & You, S.-L. Transition-metal-catalyzed asymmetric allylic dearomatization reactions. Acc. Chem. Res. 47, 2558–2573 (2014).
Article CAS PubMed Google Scholar
Zheng, C. & You, S.-L. Catalytic asymmetric dearomatization (CADA) reaction-enabled total synthesis of indole-based natural products. Nat. Prod. Rep. 36, 1589–1605 (2019).
Article CAS PubMed Google Scholar
Liu, Y.-Z., Song, H., Zheng, C. & You, S.-L. Cascade asymmetric dearomative cyclization reactions via transition-metal-catalysis. Nat. Synth. 1, 203–216 (2022).
Zhu, M., Zhang, X., Zheng, C. & You, S.-L. Energy-transfer-enabled dearomative cycloaddition reactions of indoles/pyrroles via excited-state aromatics. Acc. Chem. Res. 55, 2510–2525 (2022).
Article CAS PubMed Google Scholar
Jiang, R., Ding, L., Zheng, C. & You, S.-L. Iridium-catalyzed Z-retentive asymmetric allylic substitution reactions. Science 371, 380–386 (2021).
Article CAS PubMed Google Scholar
Tu, H.-F., Zhang, X., Zheng, C., Zhu, M. & You, S.-L. Enantioselective dearomative prenylation of indole derivatives. Nat. Catal. 1, 601–608 (2018).
Zhang, Y.-Q. et al. Asymmetric dearomatization catalysed by chiral Brønsted acids via activation of ynamides. Nat. Chem. 13, 1093–1100 (2021).
Article CAS PubMed Google Scholar
Zhang, W.-Y., Wang, H.-C., Wang, Y., Zheng, C. & You, S.-L. Asymmetric dearomatization of indoles with azodicarboxylates via cascade electrophilic amination/aza-Prins cyclization/phenonium-like rearrangement. J. Am. Chem. Soc. 145, 11745–11753 (2023).
Beletskaya, I. P., Nájera, C. & Yus, M. Stereodivergent catalysis. Chem. Rev. 118, 5080–5200 (2018).
Article CAS PubMed Google Scholar
Cao, W., Feng, X. & Liu, X. Reversal of enantioselectivity in chiral metal complex-catalyzed asymmetric reactions. Org. Biomol. Chem. 17, 6538–6550 (2019).
Article CAS PubMed Google Scholar
Jurczyk, J. et al. Single-atom logic for heterocycle editing. Nat. Synth. 1, 352–364 (2022).
Article PubMed PubMed Central Google Scholar
Peplow, M. ‘Almost magical’: chemists can now move single atoms in and out of a molecule’s core. Nature 618, 21–24 (2023).
Article CAS PubMed Google Scholar
Liu, Z., Sivaguru, P., Ning, Y., Wu, Y. & Bi, X. Skeletal editing of (hetero) arenes using carbenes. Chem. Eur. J. 29, e202301227 (2023).
Article CAS PubMed Google Scholar
Joynson, B. W. & Ball, L. T. Skeletal editing: interconversion of arenes and heteroarenes. Helv. Chim. Acta. 106, e202200182 (2023).
Roque, J. B., Kuroda, Y., Göttemann, L. T. & Sarpong, R. Deconstructive diversification of cyclic amines. Nature 564, 244–248 (2018).
Article CAS PubMed PubMed Central Google Scholar
Jurczyk, J. et al. Photomediated ring contraction of saturated heterocycles. Science 373, 1004–1012 (2021).
Article CAS PubMed PubMed Central Google Scholar
Bartholomew, G. L., Carpaneto, F. & Sarpong, R. Skeletal editing of pyrimidines to pyrazoles by formal carbon deletion. J. Am. Chem. Soc. 144, 22309–22315 (2022).
Article CAS PubMed PubMed Central Google Scholar
Wright, B. A. et al. Skeletal editing approach to bridge-functionalized bicyclo[1.1.1]pentanes from azabicyclo[2.1.1]hexanes. J. Am. Chem. Soc. 145, 10960–10966 (2023).
Article CAS PubMed PubMed Central Google Scholar
Kennedy, S. H., Dherange, B. D., Berger, K. J. & Levin, M. D. Skeletal editing through direct nitrogen deletion of secondary amines. Nature 593, 223–227 (2021).
Article CAS PubMed Google Scholar
Dherange, B. D., Kelly, P. Q., Liles, J. P., Sigman, M. S. & Levin, M. D. Carbon atom insertion into pyrroles and indoles promoted by chlorodiazirines. J. Am. Chem. Soc. 143, 11337–11344 (2021).
Article CAS PubMed PubMed Central Google Scholar
Woo, J. et al. Scaffold hopping by net photochemical carbon deletion of azaarenes. Science 376, 527–532 (2022).
Article CAS PubMed PubMed Central Google Scholar
Hyland, E. E., Kelly, P. Q., McKillop, A. M., Dherange, B. D. & Levin, M. D. Unified access to pyrimidines and quinazolines enabled by N–N cleaving carbon atom insertion. J. Am. Chem. Soc. 144, 19258–19264 (2022).
Article CAS PubMed PubMed Central Google Scholar
Pearson, T. J. et al. Aromatic nitrogen scanning by ipso-selective nitrene internalization. Science 381, 1474–1479 (2023).
Article CAS PubMed PubMed Central Google Scholar
Woo, J., Colin Stein, C., Christian, A. H. & Levin, M. D. Carbon-to-nitrogen single-atom transmutation of azaarenes. Nature 623, 77–82 (2023).
Article CAS PubMed PubMed Central Google Scholar
Reisenbauer, J. C., Green, O., Franchino, A., Finkelstein, P. & Morandi, B. Late-stage diversification of indole skeletons through nitrogen atom insertion. Science 377, 1104–1109 (2022).
Article CAS PubMed Google Scholar
Zhong, H. et al. Skeletal metalation of lactams through a carbonyl-to-nickel-exchange logic. Nat. Commun. 14, 5273 (2023).
Article CAS PubMed PubMed Central Google Scholar
Joynson, B. W., Cumming, G. R. & Ball, L. T. Photochemically mediated ring expansion of indoles and pyrroles with chlorodiazirines: synthetic methodology and thermal hazard assessment. Angew. Chem. Int. Ed. 62, e202305081 (2023).
留言 (0)