Rhodium-Catalysed 1,4-Additions in Water: Synthesis of Succinic Esters and β²-Amino Acid Derivatives

Abstract

The rhodium-catalysed addition of boronic acids to α-substituted activated alkenes proceeds smoothly in water resulting in a unique synthesis of both succinic esters and β²-amino acid ­derivatives.

conjugate addition - rhodium - boronic acids - succinic esters - β²-amino acids

References

For detailed reviews, see:

<A NAME="RD08404ST-1A">1a</A> Fagnou K. Lautens M. Chem. Rev.  2003,  103:  169 

<A NAME="RD08404ST-1B">1b</A> Hayashi T. Yamasaki K. Chem. Rev.  2003,  103:  2829 

<A NAME="RD08404ST-2A">2a</A> Itooka R. Iguchi Y. Miyaura N. Chem. Lett.  2001,  722 

<A NAME="RD08404ST-2B">2b</A> Lautens M. Roy A. Fukouka K. Fagnou K. Martin-Matute B. J. Am. Chem. Soc.  2001,  123:  5538 

<A NAME="RD08404ST-3A">3a</A> Chapman CJ. Frost CG. Adv. Synth. Catal.  2003,  345:  353 

<A NAME="RD08404ST-3B">3b</A> For related work with organotin and bismuth reagents see: Huang T.-S. Li C.-J. Org. Lett.  2001,  3:  2037 

<A NAME="RD08404ST-3C">3c</A> For recent work with potassium trifluoro(organo)borates see: Navarre L. Darse S. Genet J.-P. Eur. J. Org. Chem.  2004,  69 

<A NAME="RD08404ST-4A">4a</A> Fournie-Zaluski MC. Coulaud A. Bouboutou R. Chaillet P. Devin J. Waksman G. Costentin J. Roques BP. J. Med. Chem.  1985,  28:  1158 

<A NAME="RD08404ST-4B">4b</A> Moore WM. Spilburg CA. Biochemistry  1986,  25:  5189 

<A NAME="RD08404ST-4C">4c</A> Buhlmayer P. Caselli A. Fuhrer W. Goschke R. Rasetti V. Rueger H. Stanton JL. Criscione L. Wood JM. J. Med. Chem.  1988,  31:  1839 

<A NAME="RD08404ST-4D">4d</A> Iizuka K. Mamijo T. Kubota T. Akahane K. Umeyama H. Koso Y. J. Med. Chem.  1988,  31:  704 

<A NAME="RD08404ST-4E">4e</A> Harada H. Yamaguchi T. Iyobe A. Tsubaki A. Kamijo T. Iizuka K. Ogura K. Kiso Y. J. Org. Chem.  1990,  55:  1679 

<A NAME="RD08404ST-4F">4f</A> Morimoto T. Chiba M. Achiwa K. Tetrahedron Lett.  1990,  31:  261 

<A NAME="RD08404ST-4G">4g</A> Heitsch H. Henning R. Kleemann H.-W. Linz W. Nickel W.-U. Ruppert D. Urbach H. Wagner A. J. Med. Chem.  1993,  36:  2788 

<A NAME="RD08404ST-4H">4h</A> Juaristi E. Lopez-Ruiz H. Curr. Med. Chem.  1999,  6:  983 

<A NAME="RD08404ST-5">5</A> Burk MJ. Bienewald F. Harris M. Zanotti-Gerosa A. Angew. Chem. Int. Ed.  1998,  37:  1931 

<A NAME="RD08404ST-6">6</A>

All compounds have been satisfactorily characterised by ¹H NMR and ¹³C NMR. ¹H NMR data (300 MHz, CDCl₃) for 3a: δ = 2.34 (1 H, dd, J = 4.8, 16.8 Hz), 2.66 (2 H, m), 3.03 (2 H, m), 3.57 (3 H, s), 3.60 (3 H, s), 7.16 (5 H, m). Compound 3c: ¹H NMR (300 MHz, CDCl₃): δ = 2.39 (1 H, dd, J = 5.7, 17.1 Hz), 2.65 (1 H, dd, J = 8.7, 17.1 Hz), 2.88 (1 H, dd, J = 10.5, 16.8 Hz), 3.09 (2 H, m), 3.57 (3 H, s), 3.60 (3 H, s), 7.42 (2 H, m), 8.01 (2 H, m). Compound 3d: ¹H NMR (300 MHz, CDCl₃): δ = 2.33 (1 H, dd, J = 5.1, 16.8 Hz), 2.61 (2 H, m), 2.98 (2 H, m), 3.57 (3 H, s), 3.60 (3 H, s), 3.72 (3 H, s), 6.76 (2 H, d, J = 8.7 Hz), 7.00 (1 H, d, J = 8.7 Hz). Compound 3e: ¹H NMR (300 MHz, CDCl₃): δ = 2.34 (1 H, dd, J = 4.5, 16.5 Hz), 2.62 (2 H, m), 3.02 (2 H, m), 3.57 (3 H, s), 3.62 (3 H, s), 3.72 (3 H, s), 6.67 (3 H, m), 7.15 (1 H, dd, J = 9.6, 17.4 Hz). Compound 3f: ¹H NMR (300 MHz, CDCl₃): δ = 2.33 (1 H, dd, J = 4.8, 17.1 Hz), 2.66 (2 H, m), 2.97 (1 H, dd, J = 6.3, 13.2 Hz), 3.14 (1 H, m), 3.55 (3 H, s), 3.59 (3 H, s), 3.75 (3 H, s), 6.79 (2 H, m), 7.00 (1 H, d, J = 9.0 Hz), 7.15 (2 H, m). Compound 3g: ¹H NMR (300 MHz, CDCl₃): δ = 2.35 (1 H, dd, J = 5.1, 16.8 Hz), 2.63 (2 H, dd, J = 8.4, 16.8 Hz), 2.78 (2 H, dd, J = 7.5, 12.9 Hz), 3.07 (2 H, m), 3.58 (3 H, s), 3.59 (3 H, s), 7.19 (2 H, d, J = 8.4 Hz), 7.83 (2 H, d, J = 8.1 Hz). Compound 3h: ¹H NMR (300 MHz, CDCl₃): δ = 2.33 (1 H, dd, J = 4.8, 16.8 Hz), 2.58 (2 H, m), 2.85 (6 H, s), 2.99 (2 H, m), 3.56 (3 H, s), 3.61 (3 H, s), 6.60 (2 H, d, J = 8.7 Hz), 6.95 (2 H, d, J = 8.7 Hz). Compound 3i: ¹H NMR (300 MHz, CDCl₃): δ = 2.32 (3 H, m), 2.64 (1 H, dd, J = 8.7, 16.5 Hz), 2.91 (1 H, m), 3.58 (3 H, s), 3.63 (3 H, s), 6.00 (1 H, m), 6.30 (1 H, d, J = 15.6 Hz), 7.19 (4 H, s).

For selected recent examples of β²-amino acid synthesis see:

<A NAME="RD08404ST-7A">7a</A> Duursma A. Minaard AJ. Feringa BL. J. Am. Chem. Soc.  2003,  125:  3700 

<A NAME="RD08404ST-7B">7b</A> Lee H.-S. Park J.-S. Kim BM. Gellman SH. J. Org. Chem.  2003,  68:  1575 

<A NAME="RD08404ST-7C">7c</A> Seebach D. Schaeffer L. Gessier F. Bindschädler P. Jäger C. Josien D. Kopp S. Lelais G. Mahajan YR. Micuch P. Sebesta R. Schweizer BW. Helv. Chim. Acta  2003,  86:  1852 

<A NAME="RD08404ST-7D">7d</A> Sibi MP. Patil K. Angew. Chem. Int. Ed.  2004,  43:  1235 

<A NAME="RD08404ST-8">8</A> Basavaiah D. Krishnamacharyulu M. Rao J. Synth. Commun.  2000,  30:  2061 

<A NAME="RD08404ST-9">9</A>

All compounds have been satisfactorily characterised by ¹H NMR and ¹³C NMR. ¹H NMR data (300 MHz, CDCl₃) for 5a: δ = 2.85 (1 H, dd, J = 6.6, 14.1 Hz), 3.10 (1 H, dd, J = 8.7, 14.1 Hz), 3.35 (1 H, m), 3.85 (1 H, dd, J = 6.0, 13.8 Hz), 4.05 (1 H, dd, J = 8.4, 13.8 Hz), 5.00 (2 H, s), 7.10-7.25 (10 H, m), 7.67 (2 H, m), 7.78 (2 H, m). Compound 5b: ¹H NMR (300 MHz, CDCl₃): δ = 3.36 (1 H, m), 3.50 (2 H, m), 3.95 (1 H, dd, J = 4.8, 13.8 Hz), 4.15 (1 H, dd, J = 7.8, 13.8 Hz), 4.95 (2 H, s), 7.05 (2 H, dd, J = 1.7, 7.7 Hz), 7.15 (2 H, m,), 7.30 (3 H, m), 7.45 (2 H, m), 7.60-7.88 (6 H, m), 8.00 (1 H, d, J = 8.4 Hz). Compound 5c: ¹H NMR (300 MHz, CDCl₃): δ = 3.00 (1 H, dd, J = 5.9, 14.0 Hz), 3.15 (1 H, dd, J = 9.2, 14.0 Hz), 3.35 (1 H, m), 3.90 (1 H, dd, J = 6.0, 13.8 Hz), 4.08 (1 H, dd, J = 7.8, 13.8 Hz), 5.00 (2 H, s), 7.15 (2 H, m), 7.25 (3 H, m), 7.35 (1 H, m), 7.50 (1 H, d, J = 7.8 Hz), 7.70 (2 H, m), 7.85 (2 H, m), 8.00 (1 H, d, J = 8.1 Hz), 8.05 (1 H, s). Compound 5d: ¹H NMR (300 MHz, CDCl₃): δ 2.80 (1 H, dd, J = 6.6, 13.8 Hz), 3.00 (1 H, dd, J = 8.6, 14.0 Hz), 3.30 (1 H, m), 3.75 (3 H, s), 3.85 (1 H, dd, J = 6.0, 13.8 Hz), 4.05 (1 H, dd, J = 8.3, 13.7 Hz), 5.00 (2 H, s), 6.75 (2 H, d, J = 8.7 Hz), 7.05 (2 H, d, J = 8.7 Hz), 7.15 (2 H, m), 7.23 (3 H, m), 7.68 (2 H, m), 7.78 (2 H, m). Compound 5g: ¹H NMR (300 MHz, CDCl₃): δ = 2.55 (3 H, s), 2.95 (1 H, dd, J = 6.3, 14.1 Hz), 3.15 (1 H, dd, J = 8.7, 14.1 Hz), 3.35 (1 H, m), 3.90 (1 H, dd, J = 6.2, 14.0 Hz), 4.05 (1 H, dd, J = 8.1, 13.8 Hz), 5.00 (2 H, s), 7.15 (2 H, m), 7.18-7.28 (5 H, m), 7.70 (2 H, m), 7.78 (4 H, m). Compound 5j: ¹H NMR (300 MHz, CDCl₃): δ = 2.80 (1 H, dd, J = 6.5, 14.0 Hz), 3.00 (1 H, dd, J = 9.0, 14.1 Hz), 3.30 (1 H, m), 3.90 (1 H, dd, J = 6.3, 13.8 Hz), 4.05 (1 H, dd, J = 8.1, 13.8 Hz), 5.00 (2 H, s), 7.05 (2 H, d, J = 8.4 Hz), 7.15 (2 H, m), 7.23 (3 H, m), 7.29 (2 H, d, J = 8.4 Hz), 7.70 (2 H, m), 7.80 (2 H, m).

<A NAME="RD08404ST-10">10</A> Calmes M. Daunis J. Mai N. Tetrahedron: Asymmetry  1997,  1641 

<A NAME="RD08404ST-11">11</A> Hayashi T. Takahashi M. Takaya Y. Ogasawara M. J. Am. Chem. Soc.  2002,  124:  5052 

For examples of enantioselective additions to α,β-dehydroamino acid derivatives, see:

<A NAME="RD08404ST-12A">12a</A> Reetz MT. Moulin D. Gosburg A. Org. Lett.  2001,  3:  4083 

<A NAME="RD08404ST-12B">12b</A> Chapman CJ. Wadsworth KJ. Frost CG. J. Organomet. Chem.  2003,  680:  206 

<A NAME="RD08404ST-12C">12c</A> Navarre L. Darses S. Genet J.-P. Angew. Chem. Int. Ed.  2004,  43:  719 

<A NAME="RD08404ST-13">13</A> Dixon JA. Neiswender DD. J. Org. Chem.  1960,  25:  499