Abstract
Palladium-catalyzed intramolecular aryl etherification reaction
using bulky binaphthylphosphane ligand is shown to be a convenient
method for the synthesis of seven-membered heterocycles. Application
of this methodology to a naturally occurring proteinogenic l -amino acid has led to the synthesis of
optically active benzoxazepine ring systems of versatile biological
importance.
Key words
amino acids - palladium - ligand - etherification - chiral benzoxazepines
References
1a Sassa T.
Niwa G.
Unno H.
Ikeda M.
Miura Y.
Tetrahedron
Lett.
1974,
3941
1b Suzuki K.
Nozawa K.
Udagawa S.-I.
Kawai S.
Nakajima K.-I.
Phytochemistry
1991,
30:
2096
1c Horton DA.
Bourne GT.
Smythe ML.
Chem. Rev.
2003,
103:
893
1d Welmaker GS.
Sabalski JE.
Tetrahedron
Lett.
2004,
45:
4851
1e Costantino L.
Barlocco D.
Curr. Med. Chem.
2006,
13:
65
1f Lee S.-C.
Park SB.
Chem. Commun.
2007,
3714
2a Evans BE.
Rittle KE.
Bock MG.
DiPardo RM.
Freidinger RM.
Whitter WL.
Lundell GF.
Veber DF.
Anderson PS.
Chang RSL.
Lotti VJ.
Carino DJ.
Chen TB.
Kling PJ.
Kunkel KA.
Springes JP.
Hirshfield J.
J.
Med. Chem.
1988,
31:
2235
2b Nicolaou KC.
Pfefferkorn JA.
Roecker AJ.
Cao G.-Q.
Barluenga S.
Mitchell HJ.
J.
Am. Chem. Soc.
2000,
122:
9939
2c Barluenga J.
Valdes C.
Chem. Commun.
2005,
4891
3 Kudzma LV.
Evans SM.
Turnbull SP.
Severnak SA.
Ezell EF.
Bioorg. Med. Chem.
Lett.
1995,
5:
1177
4 Toscano L.
Grisanti G.
Fioriello G.
Seghetti E.
Bianchetti A.
Bossoni G.
Riva M.
J.
Med. Chem.
1976,
19:
208
5a Press JB.
Hofmann CM.
Eudy NH.
Day IP.
Greenblatt EN.
Safir SR.
J. Med. Chem.
1981,
24:
154
5b Liegeois JFF.
Rogister FA.
Bruhwyler J.
Damas J.
Nguyen TP.
Inarejos MO.
Chleide EMG.
Mercier MGA.
Delarge JE.
J. Med. Chem.
1994,
37:
519
5c Kohra T.
Tanaka H.
Kimura K.
Horiuchi H.
Seio K.
Arita M.
Fujimoto T.
Yamamoto I.
J. Heterocycl. Chem.
2002,
39:
163
6a Standridge RT. inventors; US Patent 4125 538.
; Chem. Abstr. 1979 , 90 , 72246r
6b Grunewald GL.
Dahanukar VH.
Ching P.
Criscione KR.
J.
Med. Chem.
1996,
39:
3539
7a Díaz-Gavilán M.
Rodríguez-Serrano F.
Gómez-Vidal JA.
Marchal JA.
Aránega A.
Gallo MA.
Espinosa A.
Campos JM.
Tetrahedron
2004,
60:
11547
7b Samanta K.
Chakravarti B.
Mishra JK.
Dhar Dwivedi SK.
Nayak LV.
Choudhry P.
Bid HK.
Konwar R.
Chattopadhyay N.
Panda G.
Bioorg. Med. Chem.
Lett.
2010,
20:
283
8 Swett LR.
Stein RG.
Kimura ET.
J. Med. Chem.
1972,
15:
42
9 Mishra JK.
Samanta K.
Jain M.
Dikshit M.
Panda G.
Bioorg. Med.
Chem. Lett.
2010,
20:
244
10 Miki T.
Kori M.
Mabuchi H.
Banno H.
Tozawa R.-I.
Nakamura M.
Itokawa S.
Sugiyama Y.
Yukimasa H.
Bioorg.
Med. Chem.
2002,
10:
401
11a Effland RC.
Davis L.
J.
Heterocycl. Chem.
1985,
22:
1071
11b Ouyang X.
Tamayo N.
Kiselyov AS.
Tetrahedron
1999,
55:
2827
11c Katritzky AR.
Xu Y.-J.
He H.-Y.
J.
Chem. Soc., Perkin Trans. 1
2002,
592
11d Margolis BJ.
Swidorski JJ.
Rogers BN.
J. Org. Chem.
2003,
68:
644
11e Omar-Amrani R.
Schneider R.
Fort Y.
Synthesis
2004,
2527
11f Lu S.-M.
Alper H.
11g Ma C.
Liu S.-J.
Xin L.
Falck JR.
Shin D.-S.
Tetrahedron
2006,
62:
9002
11h Yar M.
McGarrigle EM.
Aggarwal VK.
Org. Lett.
2009,
11:
257
12 Mishra JK.
Panda G.
J. Comb. Chem.
2007,
9:
321
13 Imramovsky A.
Vinšová J.
Férriz JM.
Kuneš J.
Pour M.
Dole˛al M.
Tetrahedron
Lett.
2006,
47:
5007
14a Majhi TP.
Achari B.
Chattopadhyay P.
Heterocycles
2007,
71:
1011 ; and references cited therein
14b Neogi A.
Majhi TP.
Mukhopadhyay R.
Chattopadhyay P.
J. Org. Chem.
2006,
71:
3291
14c Adhikary ND.
Chattopadhyay P.
Eur.
J. Org. Chem.
2010,
1754
15 Neogi A.
Majhi TP.
Achari B.
Chattopadhyay P.
Eur. J. Org. Chem.
2008,
330
16 Bensdira AS.
Felix CP.
Beatrice M.
Guidicelli A.
Pascal F.
Ferrand S.
Perrin M.
Lamartini RJ.
J. Org. Chem.
2003,
68:
6632
17 Peng W.
Forkin H.
Valery V.
Adv.
Synth. Cat.
2006,
348:
1079
18 Nandi A.
Mukhopadhyay R.
Chattopadhyay P.
J.
Chem. Soc., Perkin Trans. 1
2001,
3346
19 Giannis A.
Sandhoff K.
Angew. Chem., Int. Ed. Engl.
1989,
28:
218
20a Bergmeier SC.
Seth PP.
Tetrahedron Lett.
1999,
40:
6181
20b Moussa Z.
Romo D.
Synlett
2006,
3294
21 Crystal data of compound 8g : C20 H25 NO4 S,
FW = 375.47, triclinic, space group P 1, a = 6.687(4) Å, b = 7.508(5) Å, c = 10.114(6) Å, α = 75.93(4)˚, β = 88.29(4)˚, γ = 80.28(4)˚, V = 485.4(5) ų , Z = 1, T = 296(2)
K, d
calcd = 1.284
g cm-³ , F( 000) = 200.
Diffraction data were measured with Mo-Kα (λ = 0.71073 Å)
radiation at 296 K using a Bruker Kappa Apex 2 CCD system. A total
of 2595 unique reflections were measured (θmax = 28.18˚).
Data analyses were carried out with the Fast Fourier Transform program.
The structures were solved by direct methods using the SHELXS-97²²
program. Refinements were carried out
with a full matrix least squares method against F 2
using SHELXL-97.²³
Non-hydrogen
atoms were refined with anisotropic thermal parameters. The final R value was R 1 = 0.0479
and wR 2 = 0.1255
with I > 2σ (I ). Crystallographic data have been deposited
at the Cambridge Crystallographic Data Centre with reference numbers
CCDC 776221. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html [or
from the Cambridge Crystallographic Data Centre, 12 Union Road,
Cambridge CB2 1EZ, UK; fax: +44(1223)336033, E-mail: deposit@ccdc.cam.ac.uk].
22a Sheldrick GM.
SHELXS-97,
Program for Solution of Crystal Structures
University
of Göttingen;
Germany:
1997.
22b Sheldrick GM.
Acta Crystallogr., Ser. A
1990,
46:
467
23 Sheldrick GM.
SHELXL-97, Program for Refinement of Crystal
Structures
University of Göttingen;
Germany:
1997.
24 Kuwabe S.-I.
Torraca KE.
Buchwald SL.
J. Am. Chem. Soc.
2001,
123:
12202
