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Synlett 2023; 34(16): 1839-1844
DOI: 10.1055/a-2071-4411
DOI: 10.1055/a-2071-4411
synpacts
Vibrational Circular Dichroism Studies on Axially Chiral Carbodiimides and Allenes
This work was supported by KAKENHI (grant no. JP18H02093 and JP18KK0394) and the TOBE MAKI scholarship foundation (19-JA-013).
Abstract
The axial chirality of molecules with two consecutive double bonds (X=Y=Z) has not been well studied because of a lack of analytical methods and because of difficulties in their preparation in enantiomerically pure forms. This Synpacts article describes the use of vibrational circular dichroism spectroscopy to study the stereochemistry of carbodiimides and allenes. A strategy to obtain carbodiimides with one-handed chirality by using conformationally restrained frameworks is also discussed.
1 Introduction
2 Carbodiimides with Partially Biased Axial Chirality and One-Handed Axial Chirality
3 Axially Chiral Allenes
4 Conclusions
Key words
vibrational circular dichroism - carbodiimides - allenes - axial chirality - structural analysisPublication History
Received: 28 February 2023
Accepted after revision: 11 April 2023
Accepted Manuscript online:
11 April 2023
Article published online:
10 May 2023
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References
- 1a He Y, Wang B, Dukor RK, Nafie LA. Appl. Spectrosc. 2011; 65: 699
- 1b Batista JM. Jr, Blanch EW, de Silva Bolzani V. Nat. Prod. Rep. 2015; 32: 1280
- 1c Mándi A, Kurtán T. Nat. Prod. Rep. 2019; 36: 889
- 1d Merten C, Golub TP, Kreienborg NM. J. Org. Chem. 2019; 84: 8797
- 1e Polavarapu PL, Santoro E. Nat. Prod. Rep. 2020; 37: 1661
- 2a Krohn K, Kouam SF, Kuigoua GM, Hussain H, Cludius-Brandt S, Flörke U, Kurtán T, Pescitelli G, Di Bari L, Draeger S, Schulz B. Chem. Eur. J. 2009; 15: 12121
- 2b Felippe LG, Batista JM. Jr, Baldoqui DC, Nascimento IR, Kato MJ, He Y, Nafie LA, Furlan M. Org. Biomol. Chem. 2012; 10: 4208
- 3 Taniguchi T, Monde K, Nakanishi K, Berova N. Org. Biomol. Chem. 2008; 6: 4399
- 4 Monde K, Taniguchi T, Miura N, Vairappan CS, Suzuki M. Tetrahedron Lett. 2006; 47: 4389
- 5 Taniguchi T, Ida N, Kitahara T, Agbo DO, Monde K. Chem. Commun. 2022; 58: 6116
- 6a Taniguchi T, Nakano K, Baba R, Monde K. Org. Lett. 2017; 19: 404
- 6b Zubir MZ. M, Maulida NF, Abe Y, Nakamura Y, Abdelrasoul M, Taniguchi T, Monde K. Org. Biomol. Chem. 2022; 20: 1067
- 7 Hoffmann-Röder A, Krause N. Angew. Chem. Int. Ed. 2004; 43: 1196
- 8 Taniguchi T, Mutmainah Mutmainah, Takimoto S, Suzuki T, Watanabe S, Matsuda F, Umezawa T, Monde K. Org. Biomol. Chem. 2023; 21: 569
- 9 van’t Hoff JH. La Chimie dans L’Espace . P. M. Bazendijk; Rotterdam: 1875
- 10 Maitland P, Mills WH. Nature 1935; 135: 994
- 11 Roll LJ, Adams R. J. Am. Chem. Soc. 1932; 54: 2494
- 12a Schlögl K, Mechtler H. Angew. Chem., Int. Ed. Engl. 1966; 5: 596
- 12b Červinka O, Dudek V, Senft V. Collect. Czech. Chem. Commun. 1978; 43: 1087
- 12c Červinka O, Dudek V, Štíhel Z, Zikmund J. Collect. Czech. Chem. Commun. 1979; 44: 2843
- 13a Damrauer R, Lin H, Damrauer NH. J. Org. Chem. 2014; 79: 3781
- 13b Taniguchi T, Suzuki T, Satoh H, Shichibu Y, Konishi K, Monde K. J. Am. Chem. Soc. 2018; 140: 15577
- 14a Taniguchi T, Monde K. J. Am. Chem. Soc. 2012; 134: 3695
- 14b Komori K, Taniguchi T, Mizutani S, Monde K, Kuramochi K, Tsubaki K. Org. Lett. 2014; 16: 1386
- 14c Katakami C, Kamo S, Torii A, Hara N, Imai Y, Taniguchi T, Monde K, Okabayashi Y, Hosokai T, Kuramochi K, Tsubaki K. J. Org. Chem. 2018; 83: 14610
- 15 Anet FA. L, Jochims JC, Bradley CH. J. Am. Chem. Soc. 1970; 92: 2557
- 16a Abbate S, Lebon F, Lepri S, Longhi G, Gangemi R, Spizzichino S, Bellachioma G, Ruzziconi R. ChemPhysChem 2011; 12: 3519
- 16b Merten C, Pollok CH, Liao S, List B. Angew. Chem. Int. Ed. 2015; 54: 8841
- 16c Taniguchi T. Bull. Chem. Soc. Jpn. 2017; 90: 1005
- 16d Yang Y, Krin A, Cai X, Poopari MR, Zhang Y, Cheeseman JR, Xu Y. Molecules 2023; 28: 771
- 17a Annamalai A, Jalkanen KJ, Narayanan U, Tissot MC, Keiderling TA, Stephens PJ. J. Phys. Chem. 1990; 94: 194
- 17b Rode JE, Dobrowolski JC. J. Mol. Struct.: THEOCHEM 2003; 635: 151
- 17c O’Connor TJ, Mai BK, Nafie J, Liu P, Toste FD. J. Am. Chem. Soc. 2021; 143: 13759
- 17d Narayanan U, Keiderling TA, Elsevier CJ, Vermeer P, Runge W. J. Am. Chem. Soc. 1988; 110: 4133
- 17e Narayanan U, Keiderling TA. J. Am. Chem. Soc. 1988; 110: 4139
- 17f Kuehnel MF, Schlöder T, Riedel S, Nieto-Ortega B, Ramírez FJ, López Navarrete JT, Casado J, Lentz D. Angew. Chem. Int. Ed. 2012; 51: 2218
- 17g Abbate S, Longhi G, Gangemi F, Gangemi R, Superchi S, Caporusso AM, Ruzziconi R. Chirality 2011; 23: 841
- 17h Ma S, Tsui H.-W, Spinelli E, Busacca CA, Franses EI, Wang N.-HL, Wu L, Lee H, Senanayake C, Yee N, Gonella N, Fandrick K, Grinberg N. J. Chromatogr. A 2014; 1362: 119
- 18 Fukuzawa A, Kurosawa E. Tetrahedron Lett. 1979; 20: 2797
- 19 Umezawa T, Oguri Y, Matsuura H, Yamazaki S, Suzuki M, Yoshimura E, Furuta T, Nogata Y, Serisawa Y, Matsuyama-Serisawa K, Abe T, Matsuda F, Suzuki M, Okino T. Angew. Chem. Int. Ed. 2014; 53: 3909