Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Synlett 2022; 33(12): 1103-1107
DOI: 10.1055/a-1787-1429
DOI: 10.1055/a-1787-1429
synpacts
Phosphorus(III)-Promoted 1,2-Boronate Migration and Application to Stereoselective gem-C,B-Glycosylation
We acknowledge financial support from the National Natural Science Foundation of China (NSFC 22071262), the Shanghai Rising-Star program (20QA1411300), CAS Key Laboratory of Synthetic Chemistry of Natural Substances, and the Shanghai Institute of Organic Chemistry.
Abstract
Modifications of glycosidic linkers are valuable in medicinal chemistry and natural-product synthesis. Whereas considerable attention has been paid to the development of methods for monoglycosylation, the corresponding geminal diglycosylation has almost been ignored. Little work has focused on exploring new routes for stereoselective gem-diglycosylation, presumably due to challenges in controlling selectivity and activity on a confined quaternary carbon center. Highlighted herein is a recent advance in stereoselective C,B-glycosylation through an unprecedented PPh3-promoted 1,2-boronate-migration process.
Key words
diglycosylation - boronate migration - phosphonium ylides - C,B-glycosylation - stereoselectivityPublication History
Received: 24 February 2022
Accepted after revision: 03 March 2022
Accepted Manuscript online:
03 March 2022
Article published online:
24 March 2022
© 2022. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1a Bokor É, Kun S, Goyard D, Tóth M, Praly J.-P, Vidal S, Somsák L. Chem. Rev. 2017; 117: 1687
- 1b Yang Y, Yu B. Chem. Rev. 2017; 117: 12281
- 1c Bennett CS, Galan MC. Chem. Rev. 2018; 118: 7931
- 1d Liao H, Ma J, Yao H, Liu X.-W. Org. Biomol. Chem. 2018; 16: 1791
- 1e Nielsen MM, Pedersen CM. Chem. Rev. 2018; 118: 8285
- 1f Kulkarni SS, Wang C.-C, Sabbavarapu NM, Podilapu AR, Liao P.-H, Hung S.-C. Chem. Rev. 2018; 118: 8025
- 1g Adero PO, Amarasekara H, Wen P, Bohé L, Crich D. Chem. Rev. 2018; 118: 8242
- 1h Hettikankanamalage AA, Lassfolk R, Ekholm FS, Leino R, Crich D. Chem. Rev. 2020; 120: 7104
- 1i Dimakos V, Taylor MS. Org. Biomol. Chem. 2021; 19: 514
- 2a Ling J, Bennett CS. Angew. Chem. Int. Ed. 2020; 59: 4304
- 2b Mayfield AB, Metternich JB, Trotta AH, Jacobsen EN. J. Am. Chem. Soc. 2020; 142: 4061
- 2c Sati GC, Martin JL, Xu Y, Malakar T, Zimmerman PM, Montgomery J. J. Am. Chem. Soc. 2020; 142: 7235
- 2d Lv W, Chen Y, Wen S, Ba D, Cheng G. J. Am. Chem. Soc. 2020; 142: 14864
- 2e Zhu F, Walczak MA. J. Am. Chem. Soc. 2020; 142: 15127
- 2f Xu C, Rao VU. B, Weigen J, Loh CC. J. Nat. Commun. 2020; 11: 4911
- 2g Fu Y, Bernasconi L, Liu P. J. Am. Chem. Soc. 2021; 143: 1577
- 2h Hoang KM, Lees NR, Herzon SB. J. Am. Chem. Soc. 2021; 143: 2777
- 2i Zhao G, Yao W, Kevlishvili I, Mauro JN, Liu P, Ngai M.-Y. J. Am. Chem. Soc. 2021; 143: 8590
- 2j Zhu Y, Delbianco M, Seeberger PH. J. Am. Chem. Soc. 2021; 143: 9758
- 2k Liu Y.-H, Xia Y.-N, Gulzar T, Wei B, Li H, Zhu D, Hu Z, Xu P, Yu B. Nat. Commun. 2021; 12: 4924
- 2l Ma X, Zheng Z, Fu Y, Zhu X, Liu P, Zhang L. J. Am. Chem. Soc. 2021; 143: 11908
- 2m Zhang Y, He H, Chen Z, Huang Y, Xiang G, Li P, Yang X, Lu G, Xiao G. Angew. Chem. Int. Ed. 2021; 60: 12597
- 2n Wan L.-Q, Zhang X, Zou Y, Shi R, Cao J.-G, Xu S.-Y, Deng L.-F, Zhou L, Gong Y, Shu X, Lee GY, Ren H, Dai L, Qi S, Houk KN, Niu D. J. Am. Chem. Soc. 2021; 143: 11919
- 3 Bera S, Chatterjee B, Mondal D. RSC Adv. 2016; 6: 77212
- 4a Komura N, Kato K, Udagawa T, Asano S, Tanaka H.-N, Imamura A, Ishida H, Kiso M, Ando H. Science 2019; 364: 677
- 4b Denmark SE, Regens CS, Kobayashi T. J. Am. Chem. Soc. 2007; 129: 2774
- 4c Wang M, Zhang L, Huo X, Zhang Z, Yuan Q, Li P, Chen J, Zou Y, Wu Z, Zhang W. Angew. Chem. Int. Ed. 2020; 59: 20814
- 4d Patel NR, Nawrat CC, McLaughlin M, Xu Y, Huffman MA, Yang H, Li H, Whittaker AM, Andreani T, Lévesque F, Fryszkowska A, Brunskill A, Tschaen DM, Maloney KM. Org. Lett. 2020; 22: 4659
- 5a Vijayasaradhi S, Aidhen IS. Org. Lett. 2002; 4: 1739
- 5b Mondal D, Schweizer F. Synlett 2008; 2475
- 5c Liu H, Zhang Y, Wei R, Andolina G, Li X. J. Am. Chem. Soc. 2017; 139: 13420
- 6a Noel A, Delpech B, Crich D. Org. Lett. 2012; 14: 1342
- 6b Chen Y.-B, Liu S.-H, Hsieh M.-T, Chang C.-S, Lin C.-H, Chen C.-Y, Chen P.-Y, Lin H.-C. J. Org. Chem. 2016; 81: 3007
- 6c Kleski KA, Shi M, Lohman M, Hymel GT, Gattoji VK, Andreana PR. J. Org. Chem. 2020; 85: 16207
- 6d He H, Wu Y, Huang Y, Li X, Wang R, Yang J.-S, Liu X.-Y, Qin Y. Org. Chem. Front. 2021; 8: 2263
- 6e Zhang Z, Xu Z, Liu X, Luo S, Li T. Org. Lett. 2021; 23: 6090
- 7a Soengas RG. Tetrahedron: Asymmetry 2010; 21: 2249
- 7b Sridhar PR, Seshadri K, Madhusudhan Reddy G. Chem. Commun. 2012; 48: 756
- 7c Ramakrishna B, Sridhar PR. Org. Lett. 2013; 15: 4474
- 7d Tardieu D, Desnoyers M, Laye C, Hazelard D, Kern N, Compain P. Org. Lett. 2019; 21: 7262
- 8a Matteson DS. J. Org. Chem. 2013; 78: 10009
- 8b Armstrong RJ, Aggarwal VK. Synthesis 2017; 49: 3323
- 8c Sandford C, Aggarwal VK. Chem. Commun. 2017; 53: 5481
- 8d Namirembe S, Morken JP. Chem. Soc. Rev. 2019; 48: 3464
- 8e Kischkewitz M, Friese FW, Studer A. Adv. Synth. Catal. 2020; 362: 2077
- 8f Wang H, Jing C, Noble A, Aggarwal VK. Angew. Chem. Int. Ed. 2020; 59: 16859
- 9a Burns M, Essafi S, Bame JR, Bull SP, Webster MP, Balieu S, Dale JW, Butts CP, Harvey JN, Aggarwal VK. Nature 2014; 513: 183
- 9b Zhang L, Lovinger GJ, Edelstein EK, Szymaniak AA, Chierchia MP, Morken JP. Science 2016; 351: 70
- 9c Kischkewitz M, Okamoto K, Mück-Lichtenfeld C, Studer A. Science 2017; 355: 936
- 9d Fawcett A, Biberger T, Aggarwal VK. Nat. Chem. 2019; 11: 117
- 9e Law C, Kativhu E, Wang J, Morken JP. Angew. Chem. Int. Ed. 2020; 59: 10311
- 9f You C, Studer A. Angew. Chem. Int. Ed. 2020; 59: 17245
- 9g Davis CR, Luvaga IK, Ready JM. J. Am. Chem. Soc. 2021; 143: 4921
- 9h Simlandy AK, Brown MK. Angew. Chem. Int. Ed. 2021; 60: 12366
- 9i Xie Q, Dong G. J. Am. Chem. Soc. 2021; 143: 14422
- 9j Sharma HA, Essman JZ, Jacobsen EN. Science 2021; 374: 752
- 10a Aggarwal VK, Fang GY, Schmidt AT. J. Am. Chem. Soc. 2005; 127: 1642
- 10b Fang GY, Wallner OA, Di Blasio N, Ginesta X, Harvey JN, Aggarwal VK. J. Am. Chem. Soc. 2007; 129: 14632
- 10c Fang GY, Aggarwal VK. Angew. Chem. Int. Ed. 2007; 46: 359
- 10d Howells D, Robiette R, Fang GY, Knowles LS, Woodrow MD, Harvey JN, Aggarwal VK. Org. Biomol. Chem. 2008; 6: 1185
- 11a Argintaru OA, Ryu D, Aron I, Molander GA. Angew. Chem. Int. Ed. 2013; 52: 13656
- 11b Neu RC, Jiang C, Stephan DW. Dalton Trans. 2013; 42: 726
- 11c Molander GA, Ryu D. Angew. Chem. Int. Ed. 2014; 53: 14181
- 11d Jonker SJ. T, Jayarajan R, Kireilis T, Deliaval M, Eriksson L, Szabó KJ. J. Am. Chem. Soc. 2020; 142: 21254
- 11e Yang Y, Tsien J, Hughes JM. E, Peters BK, Merchant RR, Qin T. Nat. Chem. 2021; 13: 950
- 12 Aggarwal VK, Harvey JN, Robiette R. Angew. Chem. Int. Ed. 2005; 44: 5468
- 13 Zhao W.-C, Li R.-P, Ma C, Liao Q.-Y, Wang M, He Z.-T. J. Am. Chem. Soc. 2022; 144: 2460
- 14 Epstein WW, Garrossian M. Phosphorus Sulfur Relat. Elem. 1988; 35: 349
- 15 Li Y, Wu D, Cheng H.-G, Yin G. Angew. Chem. Int. Ed. 2020; 59: 7990
- 16a Orlandi M, Hilton MJ, Yamamoto E, Toste FD, Sigman MS. J. Am. Chem. Soc. 2017; 139: 12688
- 16b Bergmann AM, Dorn SK, Smith KB, Logan KM, Brown MK. Angew. Chem. Int. Ed. 2019; 58: 1719
- 16c Jeon J, Ryu H, Lee C, Cho D, Baik M.-H, Hong S. J. Am. Chem. Soc. 2019; 141: 10048
- 16d Wang W, Ding C, Yin G. Nat. Catal. 2020; 3: 951
- 16e Sun S.-Z, Talavera L, Spieß P, Day CS, Martin R. Angew. Chem. Int. Ed. 2021; 60: 11740
- 17 Su W, Gong T.-J, Zhang Q, Zhang Q, Xiao B, Fu Y. ACS Catal. 2016; 6: 6417