On the Synthesis of a Novel Chiral Phosphorodiamidic Acid Containing­ the α-Phenylethyl Moiety: Insights on its Conformation and Reactivity

Carlos Cruz-Hernández; Eusebio Juaristi

doi:10.1055/a-1689-3626

Synthesis, Table of Contents

Synthesis 2022; 54(17): 3801-3808
DOI: 10.1055/a-1689-3626

special topic

Special Issue in memory of Prof. Ferenc Fülöp

On the Synthesis of a Novel Chiral Phosphorodiamidic Acid Containing the α-Phenylethyl Moiety: Insights on its Conformation and Reactivity

Carlos Cruz-Hernández∗

^aDepartamento de Química, Centro de Investigación y de Estudios Avanzados, Avenida IPN No. 2508, 07360 Ciudad de México, México

,

Eusebio Juaristi∗

^aDepartamento de Química, Centro de Investigación y de Estudios Avanzados, Avenida IPN No. 2508, 07360 Ciudad de México, México

^bEl Colegio Nacional, Luis González Obregón No. 23, Centro Histórico, 06020 Ciudad de México, México

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Abstract

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Dedicated to the memory of Professor Ferenc Fülöp, friend and colleague

Abstract

A few years ago, the synthesis of chiral phosphoric acids supported on chiral BINOL frameworks was accomplished by T. Akiyama and M. Terada. Subsequent relevant applications demonstrated the importance of chiral phosphoric acids as privileged chiral inducers in asymmetric organocatalysis. In the present report, we discuss the development of novel chiral phosphorodiamidic acids derived from C ₂-symmetric trans-1,2-diaminocyclohexane aliphatic frameworks. The preparation of the new chiral Brønsted acids, based on the intermediacy of a 1,3,2-diheterophospholan-2-oxide moiety, turned out to be challenging since several plausible synthetic methodologies proved to be ineffective. Furthermore, the five-membered heterocyclic moiety turned out to be easily hydrolyzed when exposed to nucleophilic alcohols or water. Complementary to the successful multistep synthesis reported here, it was possible to obtain crystals of the key precursor of the desired phosphorodiamidic acid, which proved suitable for X-ray diffraction analysis and hence to establish important conformational characteristics of the novel heterocycle.

Key words

chiral phosphorus derivatives - α-phenylethyl moiety - chiral phosphoric acids - chiral Brønsted acids - asymmetric organocatalysis.

Full Text

References

References

1a Akiyama T, Itoh J, Fuchibe K. Adv. Synth. Catal. 2006; 348: 999
1b Kampen D, Reisinger CM, List B. Top. Curr. Chem. 2009; 291: 1
1c Akiyama T, Mori K. Chem. Rev. 2015; 115: 9277
1d Min C, Seidel D. Chem. Soc. Rev. 2017; 46: 5889
1e Rahman A, Lin X. Org. Biomol. Chem. 2018; 16: 4753
1f Oliveira V. dG, Cardoso MF. d. C, Forezi L. dS. M. Catalysts 2018; 8: 605
1g Sinibaldi A, Nori V, Baschieri A, Fini F, Arcadi A, Carlone A. Catalysts 2019; 9: 928

2a Uraguchi D, Terada M. J. Am. Chem. Soc. 2004; 126: 5356
2b Akiyama T, Itoh J, Yokota K, Fuchibe K. Angew. Chem. Int. Ed. 2004; 43: 1566

3a Taylor MS, Jacobsen EN. Angew. Chem. Int. Ed. 2006; 45: 1520
3b Nagorny P, Sun Z. Beilstein J. Org. Chem. 2016; 12: 2834

4a Huang Y, Unni AK, Thadani AN, Rawal VH. Nature 2003; 424: 146
4b Braddock DC, MacGilp ID, Perry BG. Adv. Synth. Catal. 2004; 346: 1117
4c Du H, Zhao D, Ding K. Chem. Eur. J. 2004; 10: 5964
4d Unni AK, Takenaka N, Yamamoto H, Rawal VH. J. Am. Chem. Soc. 2005; 127: 1336
4e Matsui K, Takizawa S, Sasai H. J. Am. Chem. Soc. 2005; 127: 3680

5a Sigman MS, Jacobsen EN. J. Am. Chem. Soc. 1998; 120: 4901
5b Hernández-Rodríguez M, Juaristi E. Tetrahedron 2007; 63: 7673

6a Storer RI, Aciro C, Jones LH. Chem. Soc. Rev. 2011; 40: 2330
6b Chauchan P, Mahajan S, Kaya U, Hack D, Enders D. Adv. Synth. Catal. 2015; 357: 253

7a Christ P, Lindsay AG, Vormittag SS, Neudörfl J.-M, Berkessel A, O’Donoghue AC. Chem. Eur. J. 2011; 17: 8524
7b Kaupmees K, Tolstoluzhsky N, Raja S, Rueping M, Leito I. Angew. Chem. Int. Ed. 2013; 52: 11569
7c Yang C, Xue X.-S, Jin J.-L, Li X, Cheng J.-P. J. Org. Chem. 2013; 78: 7076
7d Yang C, Xue X.-S, Li X, Cheng J.-P. J. Org. Chem. 2014; 79: 4340

8a Akiyama T. Chem. Rev. 2007; 107: 5744
8b Terada M. Synthesis 2010; 1929
8c Zamfir A, Schenker S, Freund M, Tsogoeva SB. Org. Biomol. Chem. 2010; 8: 5262
8d Parmar D, Sugiono E, Raja S, Rueping M. Chem. Rev. 2014; 114: 9047

9a Zhang J, Yu P, Li S.-Y, Sun H, Xiang S.-H, Wang J, Houk KN, Tan B. Science 2018; 361: 1087
9b Wang Q, Wang D.-X, Wang M.-X, Zhu J. Acc. Chem. Res. 2018; 51: 1290
9c Wang X.-W, Chen M.-W, Wu B, Wang B, Zhou Y.-G. J. Org. Chem. 2019; 84: 8300
9d Yang G.-H, Zhou Q, Zhang Z.-P, Zheng H.-L, Chen L, Li X. J. Org. Chem. 2019; 84: 7883
9e Chen Z, Wang L, Qian Y, Lin X. Synlett 2021; 32: 1231
9f Wang X.-W, Li X, Chen M.-W, Wu B, Zhou Y.-G. J. Org. Chem. 2021; 86: 6897
9g Hofmann F, Gärtner C, Kretzschmar M, Schneider C. Synthesis 2021; in press

10a Akiyama T, Saitoh Y, Morita H, Fuchibe K. Adv. Synth. Catal. 2005; 347: 1523
10b Rowland GB, Zhang H, Rowland EB, Chenamadhavuni S, Wang Y, Antilla JC. J. Am. Chem. Soc. 2005; 127: 15696

11 Maji R, Mallojjala SC, Wheeler SE. Chem. Soc. Rev. 2018; 47: 1142

12a Nakashima D, Yamamoto H. J. Am. Chem. Soc. 2006; 128: 9626
12b Jiao P, Nakashima D, Yamamoto H. Angew. Chem. Int. Ed. 2008; 47: 2411
12c Terada M, Sorimachi K, Uraguchi D. Synlett 2006; 133

13a Kampen D, Ladépêche A, Claßen G, List B. Adv. Synth. Catal. 2008; 350: 962
13b García-García P, Lay F, García-García P, Rabalakos C, List B. Angew. Chem. Int. Ed. 2009; 48: 4363

14a Wakchaure VN, List B. Angew. Chem. Int. Ed. 2010; 49: 4136
14b Vellalath S, Čorić I, List B. Angew. Chem. Int. Ed. 2010; 49: 9749
14c Čorić I, List B. Nature 2012; 483: 315

15a Juaristi E, Escalante J, León-Romo JL, Reyes A. Tetrahedron: Asymmetry 1998; 9: 715
15b Mastranzo VM, Santacruz E, Huelgas G, Paz E, Sosa-Rivadeneyra MV, Bernès S, Juaristi E, Quintero L, Anaya de Parrodi C. Tetrahedron: Asymmetry 2006; 17: 1663
15c Bandala Y, Juaristi E. Aldrichimica Acta 2010; 43: 65

16a Molt O, Schrader T. Synthesis 2002; 2633
16b Cruz-Hernández C, Landeros JM, Juaristi E. Synthesis of Octahydro-1,2,3-diazaphospholidine-2-oxides and their Derivatives: Applications in Asymmetric Synthesis. In Targets in Heterocyclic Systems, Vol. 23. Atannasi OA, Merino P, Spinelli D. Italian Chemical Society; Rome: 2019: 324
16c Bennani YL, Hanessian S. Tetrahedron 1996; 52: 13837

17a Hernández-Rodríguez M, Melgar-Fernández R, Juaristi E. J. Phys. Org. Chem. 2005; 18: 792
17b Seebach D, Lamatsch B, Amstutz R, Beck AK, Doler M, Egli M, Fitzi R, Gautschi M, Herradón B, Hidber PC, Irwin JJ, Locher R, Maestro M, Maeztke T, Mouriño A, Pfammatter E, Plattner DA, Schickli C, Schweizer WB, Seiler P, Stucky G, Petter W, Escalante J, Juaristi E, Quintana D, Miravitlles C, Molins E. Helv. Chim. Acta 1992; 75: 913

18 Juaristi E. Introduction to Stereochemistry and Conformational Analysis . Wiley; New York: 1991: 208-210 ; and references therein

19a Cruz-Hernández C, Hernández-González PE, Juaristi E. Synthesis 2018; 50: 1827
19b Cruz-Hernández C, Hernández-González PE, Juaristi E. Synthesis 2018; 50: 3445
19c Cruz-Hernández C, Martínez-Martínez E, Hernández-González PE, Juaristi E. Eur. J. Org. Chem. 2018; 6890

20a Olah GA, Narang SC, Balaram Gupta BG, Malhotra R. J. Org. Chem. 1979; 44: 1247
20b Olah GA, Husain A, Balaram Gupta BG, Narang SC. Angew. Chem., Int. Ed. Engl. 1981; 20: 690

21 Clark VM, Kirby GW, Todd A. J. Chem. Soc. 1958; 3039
22 Crystallographic data for (1S,2S,1′S,2′S)-5: C₂₉H₃₅O₂N₂P, Orthorhombic, P212121; a = 10.5761(4), b = 12.2777(5), c = 19.8836(9); α = 90°, β = 89.9733°, γ = 90°; V = 2581.89(19); z = 4, z′ = 1; R1 = 4.75%. CCDC 2117376 contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures

23a Cowley AH, Pinnell RP. J. Am. Chem. Soc. 1965; 87: 4454
23b Hutchins RO, Maryanoff BE, Albrand JP, Cogne A, Gagnaire D, Robert JB. J. Am. Chem. Soc. 1972; 94: 9151

24 Desiraju GR. Acc. Chem. Res. 1996; 29: 441
25 Dauber P, Hagler AT. Acc. Chem. Res. 1980; 13: 105
26 van der Knaap M, Basalan F, van der Mei HC, Busscher HJ, van der Marel GA, Overkleeft HS, Overhand M. Chem. Biodivers. 2012; 9: 2494
27 Crystallographic data for (1S,2S,1′S,2′S)-6: C₂₉H₃₅ON₂PS, Monoclinic, P21; a = 8.8328(18), b = 8.5329(17), c = 17.957(4); α = 90°, β = 99.27(3)°, γ = 90°; V = 1335.7(5); z = 2, z′ = 1; R1 = 5.14%. CCDC 2117375 contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures

28a Khorana HG, Tener GM, Wright RS, Moffatt JG. J. Am. Chem. Soc. 1957; 79: 430
28b Cherbuliez E, Probst H, Rabinowitz J. Helv. Chim. Acta 1959, 42: 1377

29a Haake PC, Westheimer FH. J. Am. Chem. Soc. 1961; 83: 1102
29b Westheimer FH. Acc. Chem. Res. 1968; 1: 70

30 Gerlt JA, Westheimer FH, Sturtevant JM. J. Biol. Chem. 1975; 250: 5059

31a Gorenstein DG, Luxon BA, Findlay JB. J. Am. Chem. Soc. 1977; 99: 8048
31b Gorenstein DG, Luxon BA, Findlay JB, Momii R. J. Am. Chem. Soc. 1977; 99: 4170
31c Gorenstein DG, Luxon BA, Findlay JB. J. Am. Chem. Soc. 1979; 101: 5869
31d Gorenstein DG, Luxon BA, Goldfield EM. J. Am. Chem. Soc. 1980; 102: 1757
31e Fanii T, Taira K, Gorenstein DG, Vaidyanathaswamy R, Verkade JG. J. Am. Chem. Soc. 1986; 108: 6311

32 Alabugin IV, Kuhn L, Medvedev MG, Krivoshchapov NV, Vil’ VA, Yaremenko IA, Mehaffy P, Yarie M, Terent’ev AO, Zolfigol MA. Chem. Soc. Rev. 2021; 50: 10253

33a Koizumi T, Arai Y, Yoshii E. Tetrahedron Lett. 1973; 48: 4763
33b Lemmen P, Richter W, Werner B, Karl R, Stumpf R, Ugi I. Synthesis 1993; 1
33c Ramirez F, Ugi I. Phosphorus, Sulfur Relat. Elem. 1976; 1: 231

34a Hudson RF, Brown C. Acc. Chem. Res. 1972; 5: 204
34b Cherkasov RA, Ovchinnikov VV, Pudovik MA, Pudovik AN. Russ. Chem. Rev. 1982; 51: 1305
34c Chang N.-Y, Lim C. J. Am. Chem. Soc. 1998; 120: 2156

35 Perrin DD, Armarego WL. F. Purification of Laboratory Chemicals . Pergamon Press; London: 1988

Supplementary Material

Supporting Information

On the Synthesis of a Novel Chiral Phosphorodiamidic Acid Containing­ the α-Phenylethyl Moiety: Insights on its Conformation and Reactivity

On the Synthesis of a Novel Chiral Phosphorodiamidic Acid Containing the α-Phenylethyl Moiety: Insights on its Conformation and Reactivity