Enantioselective Synthesis of cis- and trans-Borocyclopropylmethanol: Simple Building Blocks To Access Heterocycle-Substituted Cyclopropylmethanols

Saher H. Siddiqui; Chandrasekhar Navuluri; André B. Charette

doi:10.1055/s-0037-1611896

Synthesis, Table of Contents

Synthesis 2019; 51(20): 3834-3846
DOI: 10.1055/s-0037-1611896

paper

Enantioselective Synthesis of cis- and trans-Borocyclopropylmethanol: Simple Building Blocks To Access Heterocycle-Substituted Cyclopropylmethanols

Saher H. Siddiqui

,

Chandrasekhar Navuluri

,

André B. Charette ∗

FRQNT Centre in Green Chemistry and Catalysis, Department of Chemistry, Université de Montréal, P.O. Box 6128, Station Downtown, Montreal, Quebec, H3C 3J7, Canada Email: andre.charette@umontreal.ca

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Abstract

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Abstract

An enantioselective and non-oxidative methodology was developed to obtain enantioenriched cyclopropyl boronates using a diethanolamine-promoted selective decomplexation of dioxaborolane. The non-oxidative decomplexation of the dioxaborolane ligand from the cyclopropylmethoxide species formed in the dioxaborolane-mediated Simmons–Smith cyclopropanation reaction provided the enantioenriched CIDA-based (CIDA = N-cyclohexyliminodiacetic acid) borocyclopropane in 92% yield and 95.6:4.4 er. A robustness screen has shown diethanolamine to be compatible with esters, carbamates and N-heterocycles, providing a tool to access enantioenriched cyclopropanes carrying not only base-sensitive but oxidizable functional groups as well. Diethanolamine was found to be compatible with the modified zinco-cyclopropanation reaction of allyl alcohol to remove residual dioxaborolane from the corresponding cis-N-heterocycle cyclopropylmethanol, thereby leading to improved yields.

Key words

borocyclopropanes - heterocycles - Simmons–Smith reaction - zinco-cyclopropanation - cross-coupling

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References

References
1 Wessjohann LA, Brandt W, Thiemann T. Chem. Rev. 2003; 103: 1625
2 Talele TT. J. Med. Chem. 2016; 59: 8712
3 Knapp DM, Gillis EP, Burke MD. J. Am. Chem. Soc. 2009; 131: 6961
4 Ebner C, Carreira EM. Chem. Rev. 2017; 117: 11651
5 Volgraf M, Sellers BD, Jiang Y, Wu G, Ly CQ, Villemure E, Pastor RM, Yuen P.-w, Lu A, Luo X, Liu M, Zhang S, Sun L, Fu Y, Lupardus PJ, Wallweber HJ. A, Liederer BM, Deshmukh G, Plise E, Tay S, Reynen P, Herrington J, Gustafson A, Liu Y, Dirksen A, Dietz MG. A, Liu Y, Wang T.-M, Hanson JE, Hackos D, Scearce-Levie K, Schwarz JB. J. Med. Chem. 2016; 59: 2760

6a Tedford CE, Phillips JG, Gregory R, Panlowski GP, Fadnis L, Khan MA, Ali SM, Handley MK, Yates SL. J. Pharmacol. Exp. Ther. 1999; 289: 1160
6b Liddle J, Bamborough P, Barker MD, Campos S, Chung CW, Cousins RP. C, Faulder P, Heathcote ML, Hobbs H, Holmes DS, Ioannou C, Ramirez-Molina C, Morse MA, Osborn R, Payne JJ, Pritchard JM, Rumsey WL, Tape DT, Vicentini G, Whitworth C, Williamson RA. Bioorg. Med. Chem. Lett. 2012; 22: 5222
6c Raheem IT, Schreier JD, Fuerst J, Gantert L, Hostetler ED, Huszar S, Joshi A, Kandebo M, Kim SH, Li J, Ma B, McGaughey G, Sharma S, Shipe WD, Uslaner J, Vandeveer GH, Yan Y, Renger JJ, Smith SM, Coleman PJ, Cox CD. Bioorg. Med. Chem. Lett. 2016; 26: 126

7a Sayes M, Charette AB. Angew. Chem. Int. Ed. 2018; 57: 13514
7b Benoit G, Charette AB. J. Am. Chem. Soc. 2017; 139: 1364
7c Spencer JA, Jamieson C, Talbot EP. A. Org. Lett. 2017; 19: 3891
7d de Meijere A, Khlebnikov AF, Sünnemann HW, Frank D, Rauch K, Yufit DS. Eur. J. Org. Chem. 2010; 3295
7e Fontani P, Carboni B, Vaultier M, Carrie R. Tetrahedron Lett. 1989; 30: 4815
7f Fontani P, Carboni B, Vaultier M, Maas G. Synthesis 1991; 605
7g Fujioka Y, Amii H. Org. Lett. 2008; 10: 769
7h He J, Jiang H, Takise R, Zhu RY, Chen G, Dai HX, Dhar T, Shi J, Zhang H, Cheng PT. Angew. Chem. Int. Ed. 2016; 55: 785
7i Hussain MM, Li H, Hussain N, Ureña M, Carroll PJ, Walsh PJ. J. Am. Chem. Soc. 2009; 131: 6516
7j Liskey CW, Hartwig JF. J. Am. Chem. Soc. 2013; 135: 3375
7k Markó IE, Giard T, Sumida S, Gies A.-E. Tetrahedron Lett. 2002; 43: 2317
7l Markó IE, Kumamoto T, Giard T. Adv. Synth. Catal. 2002; 344: 1063
7m Miyamura S, Araki M, Suzuki T, Yamaguchi J, Itami K. Angew. Chem. Int. Ed. 2015; 54: 846

8a Imai T, Mineta H, Nishida S. J. Org. Chem. 1990; 55: 4986
8b Luithle JE. A, Pietruszka J. J. Org. Chem. 1999; 64: 8287

9 Carreras J, Caballero A, Pérez PJ. Angew. Chem. Int. Ed. 2018; 57: 2334
10 Zimmer LE, Charette AB. J. Am. Chem. Soc. 2009; 131: 15624

11a Charette AB, Beauchemin A. Org. React. (N.Y.) 2001; 58: 1
11b Charette AB, Juteau H. J. Am. Chem. Soc. 1994; 116: 2651

For a related preparation of cyclopropane building blocks, see:

12a Chawner SJ, Cases-Thomas MJ, Bull JA. Eur. J. Org. Chem. 2017; 5015
12b Bajaj P, Sreenilayam G, Tyagi V, Fasan R. Angew. Chem. Int. Ed. 2016; 55: 16110

13 Hohn E, Paleček J, Pietruszka J, Frey W. Eur. J. Org. Chem. 2009; 3765

14a Uno BE, Gillis EP, Burke MD. Tetrahedron 2009; 65: 3130
14b Morrill C, Grubbs RH. J. Org. Chem. 2003; 68: 6031

15a Molander GA, Biolatto B. J. Org. Chem. 2003; 68: 4302
15b Molander GA, Canturk B, Kennedy LE. J. Org. Chem. 2008; 74: 973
15c Molander GA, Gormisky PE. J. Org. Chem. 2008; 73: 7481

16 Lennox AJ. J. Organotrifluoroborate Preparation. In Organotrifluoroborate Preparation, Coupling and Hydrolysis. Springer; Heidelberg: 2013: 11-36
17 Maiti G, Roy SC. Tetrahedron Lett. 1997; 38: 495

18a Coutts SJ, Adams J, Krolikowski D, Snow RJ. Tetrahedron Lett. 1994; 35: 5109
18b Snow RJ, Bachovchin WW, Barton RW, Campbell SJ, Coutts SJ, Freeman DM, Gutheil WG, Kelly TA, Kennedy CA. J. Am. Chem. Soc. 1994; 116: 10860
18c Coutts SJ, Kelly TA, Snow RJ, Kennedy CA, Barton RW, Adams J, Krolikowski DA, Freeman DM, Campbell SJ, Ksiazek JF. J. Med. Chem. 1996; 39: 2087
18d Kinder DH, Katzenellenbogen JA. J. Med. Chem. 1985; 28: 1917
18e Matteson DS, Jesthi PK, Sadhu KM. Organometallics 1984; 3: 1284
18f Martichonok V, Jones JB. J. Am. Chem. Soc. 1996; 118: 950
18g Martin R, Jones JB. Tetrahedron Lett. 1995; 36: 8399

19 Gonzalez JA, Ogba OM, Morehouse GF, Rosson N, Houk KN, Leach AG, Cheong PH. Y, Burke MD, Lloyd-Jones GC. Nat. Chem. 2016; 8: 1067

20a Kettner CA, Shenvi AB. J. Biol. Chem. 1984; 259: 15106
20b Tripathy PB, Matteson DS. Synthesis 1990; 200
20c Sun J, Perfetti MT, Santos WL. J. Org. Chem. 2011; 76: 3571
20d Rettig SJ, Trotter J. Can. J. Chem. 1975; 53: 1393

21 Zhao J, Jonker SJ. T, Meyer DN, Schulz G, Tran CD, Eriksson L, Szabò KJ. Chem. Sci. 2018; 9: 3305
22 Collins KD, Glorius F. Nat. Chem. 2013; 5: 597

23a Bobbitt JM. Periodate Oxidation of Carbohydrates . In Advances in Carbohydrate Chemistry, Vol. 11. Wolfrom ML, Tipson RS. Elsevier; Amsterdam: 1956: 1-41
23b Copéret C, Adolfsson H, Khuong T.-AV, Yudin AK, Sharpless KB. J. Org. Chem. 1998; 63: 1740

24a Chemler SR, Trauner D, Danishefsky SJ. Angew. Chem. Int. Ed. 2001; 40: 4544
24b Miyaura N, Suzuki A. Chem. Rev. 1995; 95: 2457
24c Molander GA, Jean-Gérard L. Org. React. 2013; 79: 1

25 Gillis EP, Burke MD. Aldrichimica Acta 2009; 42: 17
26 Duncton MA. J, Singh R. Org. Lett. 2013; 15: 4284
27 Shriver DF, Drezdzon MA. The Manipulation of Air-Sensitive Compounds, 2nd ed. Wiley; New York: 1986
28 Wang K, Bates RW. Synthesis 2017; 49: 2749
29 Charette AB, Juteau H, Lebel H, Molinaro C. J. Am. Chem. Soc. 1998; 120: 11943
30 Nicolaou KC, Rhoades D, Lamani M, Pattanayak MR, Kumar SM. J. Am. Chem. Soc. 2016; 138: 7532
31 Joliton A, Plancher JM, Carreira EM. Angew. Chem. Int. Ed. 2016; 55: 2113
32 Ohtsuka N, Okuno M, Hoshino Y, Honda K. Org. Biomol. Chem. 2016; 14: 9046
33 Kumpulainen ET. T, Pohjakallio A. Adv. Synth. Catal. 2014; 356: 1555

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