Stereoselective Synthesis of (4S,5S)-5-Vinyloxazolidin-2-one-4-carboxylate as a β-Vinylserine Synthetic Equivalent by Vinyl Grignard Addition to an N-Tosyl Version of Garner’s Aldehyde

Abstract

A highly efficient synthesis of a β-vinylserine synthetic equivalent is reported that exploits the stereodirecting effect of the N-toluenesulfonamide in an anti-diastereoselective (8.5:1) vinyl Grignard addition to an analogue of Garner’s aldehyde. Both aryl and alkyl ­Grignards are shown to give increased anti-selectivity compared with N-Boc Garner’s aldehyde.

Key words

vinylserine - alkenyl amino acid - Garner aldehyde - oxazolidinones

Publication History

Received: 07 October 2020

Accepted after revision: 10 November 2020

Accepted Manuscript online:
10 November 2020

Article published online:
08 January 2021

• References and Notes

• 1 Ngo JT, Tirrell DA. Acc. Chem. Res. 2011; 44: 677
• 2a Blackwell HE, Grubbs RH. Angew. Chem. Int. Ed. 1998; 37: 3281
• 2b Schafmeister CE, Po J, Verdine GL. J. Am. Chem. Soc. 2000; 122: 5891
• 2c Aillard B, Robertson NS, Baldwin AR, Robins S, Jamieson AG. Org. Biomol. Chem. 2014; 12: 8775
• 2d Yeo DJ, Warriner SL, Wilson AJ. Chem. Commun. 2013; 49: 9131
• 3 Zhang X, van der Donk WA. J. Am. Chem. Soc. 2007; 129: 2212
• 4 Ibuka T, Habashita H, Otaka A, Fujii N, Oguchi Y, Uyehara T, Yamamoto Y. J. Org. Chem. 1991; 56: 4370
• 5a Oishi S, Narumi T, Ohno H, Otaka A, Fujii N. Yuki Gosei Kagaku Kyokaishi 2008; 66: 846
• 5b Venkatesan N, Kim BH. Curr. Med. Chem. 2002; 9: 2243
• 6a Hakogi T, Yamamoto T, Fujii S, Ikeda K, Katsumura S. Tetrahedron Lett. 2006; 47: 2627
• 6b Yamamoto T, Hasegawa H, Hakogi T, Katumura S. Org. Lett. 2006; 8: 5569
• 6c Wisse P, de Geus MA. R, Cross G, van den Nieuwendijk AM. C. H, van Rooden EJ, van den Berg RJ. B. H. N, Aerts JM. F. G, van der Marel GA, Codée JD. C, Overkleeft HS. J. Org. Chem. 2015; 80: 7258
• 7a Knight JG, Tchabanenko K. Tetrahedron 2003; 59: 281
• 7b Takahata H, Banba Y, Sasatani M, Nemoto H, Kato A, Adachi I. Tetrahedron 2004; 60: 8199
• 8 Lee D. Synlett 2012; 23: 2840
• 9 Wang B, Liu Y, Jiao R, Feng Y, Li Q, Chen C, Liu L, He G, Chen G. J. Am. Chem. Soc. 2016; 138: 3926
• 10 Murphy-Benenato KE, Dangel B, Davis HE, Durand-Réville TF, Ferguson AD, Gao N, Jahic H, Mueller JP, Manyak EL, Quiroga O, Rooney M, Sha L, Sylvester M, Wu F. Zambrowski M., Zhao S. X. 2015; 6: 537
• 11a Robertson J, Abdulmalek E. Tetrahedron Lett. 2009; 50: 3516
• 11b Kim H, Yoo D, Choi SY, Chung YK, Kim YG. Tetrahedron: Asymmetry 2008; 19: 1965
• 11c Martín R, Moyano A, Pericàs MA, Riera A. Org. Lett. 2000; 2: 93
• 11d Amador M, Ariza X, Garcia J, Sevilla S. Org. Lett. 2002; 4: 4511
• 12 Fraunhoffer KJ, White MC. J. Am. Chem. Soc. 2007; 129: 7274
• 13 Lee JH, Kang JE, Yang MS, Kang KY, Park KH. Tetrahedron 2001; 57: 10071
• 14a Kazmaier U, Pähler S, Endermann R, Häbich D, Kroll H.-P, Riedl B. Bioorg. Med. Chem. 2002; 10: 3905
• 14b Dubreuil D, Pipelier M, Micouin L, Lecourt T, Lacone V, Bonneville M, Lependu J, Turcot-Dubois A.-L. WO 2008/047249, 2008
• 15a Garner P, Park JM. J. Org. Chem. 1988; 53: 2979
• 15b Garner P. Tetrahedron Lett. 1984; 25: 5855
• 16a Passiniemi M, Koskinen AM. P. Beilstein J. Org. Chem. 2013; 9: 2641
• 16b Coleman RS, Carpenter AJ. Tetrahedron Lett. 1992; 33: 1697
• 16c Ojima I, Vidal ES. J. Org. Chem. 1998; 63: 7999
• 16d Kumar G, Kaur S, Singh V. Helv. Chim. Acta 2011; 94: 650
• 16e Ghosal P, Shaw AK. Tetrahedron Lett. 2010; 51: 4140
• 16f Bhabak KP, Proksch D, Redmer S, Arenz C. Bioorg. Med. Chem. 2012; 20: 6154
• 17 Herold J. Helv. Chim. Acta 1988; 71: 354
• 18 Ibuka T, Mimura N, Aoyama H, Akaji M, Hono H, Miwa Y, Taga T, Nakai K, Tamamura H, Fujii N, Yamamoto Y. J. Org. Chem. 1997; 62: 999
• 19a Myeong I.-S, Kim JS, Park M.-G, Jeon H.-H, Jung C, Lee Y.-T, Ham W.-H. Synthesis 2018; 50: 2058
• 19b Yamamoto T, Hasegawa H, Hakogi T, Katsumura S. Org. Lett. 2006; 8: 5569
• 19c Jin T, Mu Y, Kim J.-S, Park S.-H, Jin X, Kang J.-C, Oh C.-Y, Ham W.-H. Synth. Commun. 2014; 44: 2401
• 20a Jurczak J, Golebiowski A. Chem. Rev. 1989; 89: 149
• 20b Knight JG, Ainge SW, Harm AM, Harwood SJ, Maughan HI, Armour DR, Hollinshead DM, Jaxa-Chamiec AA. J. Am. Chem. Soc. 2000; 122: 2944
• 21a Çelebi-Ölçüm N, Lam Y.-h, Richmond E, Ling KB, Smith AD, Houk KN. Angew. Chem. Int. Ed. 2011; 50: 11478
• 21b Richmond E, Ling KB, Duguet N, Manton LB, Çelebi-Ölçüm N, Lam Y.-H, Alsancak S, Slawin AM. Z, Houk KN, Smith AD. Org. Biomol. Chem. 2015; 13: 1807
• 22 Gryko D, Urbańczyk-Lipkowska Z, Jurczak J. Tetrahedron: Asymmetry 1997; 8: 4059
• 23 Reginato G, Pezzati B, Ienco A, Manca G, Rossin A, Mordini A. J. Org. Chem. 2011; 76: 7415
• 24 N-[(1R,2S)-2-Hydroxy-1-(hydroxymethyl)but-3-en-1-yl]-4-methylbenzenesulfonamide (3) A 1.6 M solution of vinylmagnesium chloride in THF (18.9 mmol, 11.8 mL, 4 equiv) was added dropwise over 30 min to a solution of the aldehyde 8 (1.34 g, 4.74 mmol) in THF (44 mL) at –40 °C. The solution was then warmed to 0 °C and stirred overnight at rt. The solution was then poured into cold sat. aq NH₄Cl and extracted with EtOAc (×3). The combined organic extracts were washed with brine, dried (Na₂SO₄), filtered, and concentrated to give crude product 10 as a colorless viscous oil; yield: ~1.5 g. ¹H NMR (400 MHz, CDCl₃): δ = 7.85–7.72 (m, 2 H), 7.39–7.29 (m, 2 H), 5.95–5.76 (m, 1 H), 5.49–5.23 (m, 2 H), 4.47 (td, J = 5.2, 2.4 Hz, 1 H), 4.01 (dd, J = 9.2, 4.2 Hz, 1 H), 3.91–3.65 (m, 2 H), 2.82 (d, J = 5.4 Hz, 1 H), 2.46 (s, 3 H), 1.72 (s, 3 H), 1.62–1.47 (m, 3 H) To a solution of the crude vinyl alcohol 10 (~4.74 mmol) in MeOH (80 mL) and EtOH (80 mL) at r.t. was added TsOH·H₂O (180 mg 0.95 mmol, 2 equiv). The solution was stirred overnight then concentrated to half its original volume, diluted with EtOAc (400 mL), and washed with 2:1 sat. aq NaHCO₃–H₂O (100 mL). The aqueous phase was back-extracted with EtOAc, and the combined organic extracts were washed with brine (×2) and dried (Na₂SO₄). Flash column chromatography (silica gel, 50–75% EtOAc–hexanes) gave an off-white solid; yield: 1.00 g (80%); mp 75–76 °C; R_f = 0.20 (50% EtOAc–hexanes). ¹H NMR (400 MHz, CDCl₃): δ = 7.81 (d, J = 8.3 Hz, 2 H), 7.34 (d, J = 8.3 Hz, 2 H), 5.82 (ddd, J = 17.3, 10.6, 5.1 Hz, 1 H), 5.44 (d, J = 7.9 Hz, 1 H), 5.37 (bd, J = 17.2, Hz, 1 H), 5.37 (bd, J = 10.6 Hz, 1 H), 4.29 (m, 1 H), 3.86 (dt, J = 11.6, 3.6 Hz, 1 H), 3.51 (ddd, J = 11.5, 7.8, 3.8 Hz, 1 H), 3.28 (dt, J = 7.9, 3.7 Hz, 1 H), 2.54 (d, J = 10.6 Hz, 1 H), 2.46 (s, 3 H), 2.25 (dd, J = 7.8, 4.1 Hz, 1 H). ¹³C NMR (100 MHz, CDCl₃): δ = 143.8, 137.4, 136.4, 129.9, 127.1, 117.2, 74.8, 61.8, 57.3, 21.6. HRMS (ESI-TOF): m/z [M + Na]⁺ calcd for C₁₂H₁₇NNaO₄S: 294.0776; found: 294.0770.
• 25a Ageno G, Banfi L, Cascio G, Guanti G, Manghisi E, Riva R, Rocca V. Tetrahedron 1995; 51: 8121
• 25b Williams L, Zhang Z, Shao F, Carroll PJ, Joullié MM. Tetrahedron 1996; 52: 11673
• 26 Mengel A, Reiser O. Chem. Rev. 1999; 99: 1191
• 27a Malins LR, Payne RJ. Org. Lett. 2012; 14: 3142
• 27b Giltrap AM, Haeckl FP. J, Kurita KL, Linington RG, Payne RJ. J. Org. Chem. 2018; 83: 7250
• 28 Bayquen AV, Read RW. Tetrahedron 1996; 52: 13467
• 29 Knight JG, Lawson IM, Johnson CN. Synthesis 2006; 227
• 30a Myeong I.-S, Lee Y.-T, Lee S.-H, Jung C, Kim J.-S, Park S.-H, Kang J, Lee S.-J, Ye I.-H, Ham W.-H. Tetrahedron: Asymmetry 2017; 28: 1053
• 30b Zamani F, Pyne SG, Hyland CJ. T. J. Org. Chem. 2017; 82: 6819
• 31a Liu H.-J, Han I.-S. Synth. Commun. 1985; 15: 759
• 31b Laib T, Chastanet J, Zhu J. J. Org. Chem. 1998; 63: 1709