Synlett 2022; 33(12): 1103-1107 DOI: 10.1055/a-1787-1429
Phosphorus(III)-Promoted 1,2-Boronate Migration and Application to Stereoselective gem -C,B-Glycosylation
Zhi-Tao He∗
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 -
stereoselectivity
Publication History
Received: 24 February 2022
Accepted after revision: 03 March 2022
Accepted Manuscript online: 03 March 2022
Article published online: 24 March 2022
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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