Abstract
Starting from a single, chiral, bicyclic derivative of uracil, all four stereoisomers of 2-aminocyclobutanecarboxylic acid have been prepared in enantiomerically pure form, using a synthetic sequence which begins with a key photochemical [2+2] cycloaddition reaction and includes a practical cis to trans β-amino acid isomerisation procedure.
Key words
photochemistry - heterocycles - β-amino acids - cyclobutanes - stereoselective synthesis
References
1a Spiteller P.
von Nussbaum F. In Enantioselective Synthesis of β-Amino Acids
2nd ed.:
Juaristi E.
Soloshonok VA.
Wiley-VCH;
Weinheim:
2005.
p.19
1b von Nussbaum F.
Spiteller P. In
Highlights in Bioorganic Chemistry: Methods and Applications
Schmuck C.
Wennemers H.
Wiley-VCH;
Weinheim:
2004.
p.63
2a Arvidsson PI.
Ryder NS.
Weiss HM.
Hook DF.
Escalante J.
Seebach D.
Chem. Biodivers.
2005,
2:
401
2b Steer DL.
Lew RA.
Perlmutter P.
Smith AI.
Aguilar M.-I.
Curr. Med. Chem.
2002,
9:
811
2c Schreiber JV.
Frackenpohl J.
Moser F.
Fleishmann T.
Kohler H.-PE.
Seebach D.
ChemBioChem
2002,
3:
424
3a Beke T.
Somlai C.
Perczel A.
J. Comput. Chem.
2006,
27:
20
3b Martinek TA.
Fülöp F.
Eur. J. Biochem.
2003,
270:
3657
3c Cheng RP.
Gellman SH.
DeGrado WF.
Chem. Rev.
2001,
101:
3219
3d Möhle K.
Günther R.
Thormann M.
Sewald N.
Hofmann H.-J.
Biopolymers
1999,
50:
167
3e Gademann K.
Hintermann T.
Schreiber JV.
Curr. Med. Chem.
1999,
6:
905
4a Seebach D.
Beck AK.
Bierbaum DJ.
Chem. Biodivers.
2004,
1:
1111
4b Seebach D.
Kimmerlin T.
Šebesta R.
Campo MA.
Beck AK.
Tetrahedron
2004,
60:
7455
5a Juaristi E.
Soloshonok VA.
Wiley-VCH;
Weinheim:
2005.
2nd ed.
5b Liu M.
Sibi MP.
Tetrahedron
2002,
58:
7991
5c Abele S.
Seebach D.
Eur. J. Org. Chem.
2000,
1
5d Abdel-Magid F.
Cohen JH.
Maryanoff CA.
Curr. Med. Chem.
1999,
6:
955
5e Juaristi E.
López-Ruiz H.
Curr. Med. Chem.
1999,
6:
983
5f Cardillo G.
Tomasini C.
Chem. Soc. Rev.
1996,
117
6 Fülöp F.
Chem. Rev.
2001,
101:
2181
7a Kuhl A.
Hahn MG.
Dumić M.
Mittendorf J.
Amino Acids
2005,
29:
89
7b North M.
J. Peptide Sci.
2000,
6:
301
8a Hetényi A.
Mándity IM.
Martinek TA.
Tóth GK.
Fülöp F.
J. Am. Chem. Soc.
2005,
127:
547
8b Barechi JJ.
Huang X.
Appella DH.
Christianson L.
Durell SR.
Gellman SH.
J. Am. Chem. Soc.
2000,
122:
2711
8c Appella DH.
Christianson LA.
Karle IL.
Powell DR.
Gellman SH.
J. Am. Chem. Soc.
1999,
121:
6206
9a Schmitt MA.
Choi SH.
Guzei IA.
Gellman SH.
J. Am. Chem. Soc.
2005,
127:
13130
9b Hayen A.
Schmitt MA.
Ngassa FN.
Thomasson KA.
Gellman SH.
Angew. Chem. Int. Ed.
2004,
43:
505
9c Appella DH.
Christianson LA.
Klein DA.
Richards MR.
Powell DR.
Gellman SH.
J. Am. Chem. Soc.
1999,
121:
7574
9d Appella DH.
Christianson LA.
Klein DA.
Huang X.
Barchi JJ.
Powell DR.
Gellman SH.
Nature
1997,
387:
381
10a Porter EA.
Weisblum B.
Gellman SH.
J. Am. Chem. Soc.
2005,
127:
11516
10b Schmitt MA.
Weisblum B.
Gellman SH.
J. Am. Chem. Soc.
2004,
126:
6848
10c Raguse TL.
Porter EA.
Weisblum B.
Gellman SH.
J. Am. Chem. Soc.
2002,
124:
12774
10d Porter EA.
Wang X.
Lee H.-S.
Weisblum B.
Gellman SH.
Nature
2000,
404:
565
11 Pomerantz WC.
Abbott NL.
Gellman SH.
J. Am. Chem. Soc.
2006,
128:
8730
12 Martinek TA.
Tóth GK.
Vass E.
Hollósi M.
Fülöp F.
Angew. Chem. Int. Ed.
2002,
41:
1718
13a De Pol S.
Zorn C.
Klein CD.
Zerbe O.
Reiser O.
Angew. Chem. Int. Ed.
2004,
43:
511
13b Gnad F.
Reiser O.
Chem. Rev.
2003,
103:
1603
14a Izquierdo S.
Rúa F.
Sbai A.
Parella T.
Álvarez-Larena .
Branchadell V.
Ortuño RM.
J. Org. Chem.
2005,
70:
7963
14b Izquierdo S.
Martín-Vilà M.
Moglioni AG.
Branchadell V.
Ortuño RM.
Tetrahedron: Asymmetry
2002,
13:
2403
15 Izquierdo S.
Kogan MJ.
Parella T.
Moglioni AG.
Branchadell V.
Giralt E.
Ortuño RM.
J. Org. Chem.
2004,
69:
5093
16 Ortuño RM.
Moglioni AG.
Moltrasio GY.
Curr. Org. Chem.
2005,
9:
237
17a Mittendorf J.
Kunisch F.
Matzke M.
Militzer H.-C.
Schmidt A.
Schönfeld W.
Bioorg. Med. Chem. Lett.
2003,
13:
433
17b Richter LS.
Andersen S.
Tetrahedron Lett.
1998,
39:
8747
17c Yuan P.
Driscoll MR.
Raymond SJ.
Hansen DE.
Blatchly RA.
Tetrahedron Lett.
1994,
35:
6195
17d Mitsudo T.-A.
Zhang S.-W.
Satake N.
Kondo T.
Watanabe Y.
Tetrahedron Lett.
1992,
33:
5533
17e Katagiri N.
Sato H.
Kaneko C.
Chem. Pharm. Bull.
1990,
38:
288
18a Martín-Vilà M.
Muray E.
Aguado GP.
Alvarez-Larena A.
Branchadell V.
Minguillón C.
Giralt E.
Ortuño RM.
Tetrahedron: Asymmetry
2000,
11:
3569
18b Martín-Vilà M.
Minguillón C.
Ortuño RM.
Tetrahedron: Asymmetry
1998,
9:
4291
19 Bolm C.
Schiffers I.
Atodiresei I.
Hackenberger CPR.
Tetrahedron: Asymmetry
2003,
14:
3455
20a Kennewell PD.
Matharu SS.
Taylor JB.
Westwood R.
Sammes PG.
J. Chem. Soc., Perkin Trans. 1
1982,
2563
20b Cannon JG.
Rege AB.
Gruen TL.
Long JP.
J. Med. Chem.
1972,
15:
71
20c Shroff CC.
Stewart WS.
Uhm SJ.
Wheeler JW.
J. Org. Chem.
1971,
36:
3356
21a Gauzy C.
Saby B.
Pereira E.
Faure S.
Aitken DJ.
Synlett
2006,
1394
21b Aitken DJ.
Gauzy C.
Pereira E.
Tetrahedron Lett.
2002,
43:
6177
22 Brannock KC.
Bell A.
Burpitt RD.
Kelly CA.
J. Org. Chem.
1964,
29:
801
23 Basler B.
Schuster O.
Bach T.
J. Org. Chem.
2005,
70:
9798
24 Gauzy C.
Pereira E.
Faure S.
Aitken DJ.
Tetrahedron Lett.
2004,
45:
7095
25a Furutani A.
Katayama K.
Uesima Y.
Ogura M.
Tobe Y.
Kurosawa H.
Tsutsumi K.
Moriomoto T.
Kakiuchi K.
Chirality
2006,
18:
217
25b Grosch B.
Bach T.
CRC Handbook of Organic Photochemistry and Photobiology
2nd ed.:
Lenci F.
Horspool WM.
CRC Press;
New York:
2004.
p.61.1
25c Bach T.
Bergmann H.
Grosch B.
Harms K.
J. Am. Chem. Soc.
2002,
124:
7982
26 Sekine M.
J. Org. Chem.
1989,
54:
2321
27 Thibon J.
Latxague L.
Déléris G.
J. Org. Chem.
1997,
62:
4635
28 Ludek OR.
Meier C.
Eur. J. Org. Chem.
2006,
941 ; and references therein
29a Csuk R.
Eversmann L.
Tetrahedron
1998,
54:
6445
29b Frieden M.
Giraud M.
Reese CB.
Song Q.
J. Chem. Soc., Perkin Trans. 1
1998,
2827
29c Cruickshank KA.
Jiricny J.
Reese CB.
Tetrahedron Lett.
1984,
25:
681
30a Agami C.
Cheramy S.
Dechoux L.
Melaimi M.
Tetrahedron
2001,
57:
195
30b Agami C.
Cheramy S.
Dechoux L.
Kadouri-Puchot C.
Synlett
1999,
727
31a Li SS.
Sun XL.
Ogura H.
Konda Y.
Sasaki T.
Toda Y.
Takayanagi H.
Harigaya Y.
Chem. Pharm. Bull.
1995,
43:
144
31b Haga N.
Ishikawa I.
Takayanagi H.
Ogura H.
Bull. Chem. Soc. Jpn.
1994,
67:
728
31c Sun XL.
Haga N.
Ogura H.
Takayanagi H.
Chem. Pharm. Bull.
1994,
42:
2352
31d Ishikawa I.
Itoh T.
Takayanagi H.
Oshima J.-i.
Kawahara N.
Mizuno Y.
Ogura H.
Chem. Pharm. Bull.
1991,
39:
1922
31e Wexler AJ.
Balchunis RJ.
Swenton JS.
J. Org. Chem.
1984,
49:
2733
31f Wexler AJ.
Hyatt JA.
Raynolds PW.
Cottrell C.
Swenton JS.
J. Am. Chem. Soc.
1978,
100:
512
31g Wexler AJ.
Swenton JS.
J. Am. Chem. Soc.
1976,
98:
1602
31h Maleski R.
Morrison H.
Mol. Photochem.
1972,
4:
507
32a Margaretha P. In
Molecular and Supramolecular Photochemistry
Vol. 12:
Griesbeck AG.
Mattay J.
Marcel Dekker;
New York:
2005.
p.211
32b Bach T.
Synthesis
1998,
683
32c Crimmins MT.
Reinhold TL.
Org. React.
1993,
44:
297
33a Tsutsumi K.
Nakano H.
Furutani A.
Endou K.
Merpuge A.
Shintani T.
Morimoto T.
Kakiuchi K.
J. Org. Chem.
2004,
69:
785
33b Tsutsumi K.
Endou K.
Furutani A.
Ikki T.
Nakano H.
Shintani T.
Morimoto T.
Kakiuchi K.
Chirality
2003,
15:
504
33c de March P.
Figuerdo M.
Font J.
Raya J.
Tetrahedron Lett.
1999,
40:
2205
33d Tsujishima H.
Nakatani K.
Shimamato K.
Shigeri Y.
Yumoto N.
Ohfune Y.
Tetrahedron Lett.
1998,
39:
1193
33e Alibés R.
Bourdelande JL.
Font J.
Gregori A.
Parella T.
Tetrahedron
1996,
52:
1267
33f Alibés R.
Bourdelande JL.
Font J.
Tetrahedron: Asymmetry
1991,
2:
1391
33g Hoffmann N.
Scharf H.-D.
Liebigs Ann. Chem.
1991,
1273
33h Kakiuchi K.
Ue M.
Tsukahara H.
Shimizu T.
Miyao T.
Tobe Y.
Odaira Y.
Yasuda M.
Shima K.
J. Am. Chem. Soc.
1989,
111:
3707 ; supplementary material
33i Hoffmann N.
Scharf H.-D.
Runsink J.
Tetrahedron Lett.
1989,
30:
2637
33j Meyers AI.
Fleming SA.
J. Am. Chem. Soc.
1986,
108:
306
34 Crystallographic data for (-)-13a : C14 H14 N2 O2 , M = 242.27, T = 293 K, space group P 61, a = 8.3788 (4) Å, b = 8.3788 (4) Å, c = 28.4565 (17) Å, α = 90.00°, β = 90.00°, γ = 120.00°, Z = 6, V = 1730.12 (16) Å3 , ρcalcd = 1.395 g/cm-3 . Full crystallographic data have been deposited with the Cambridge Crystallographic Data Centre (CCDC) as supplementary publication number CCDC 626949. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK, fax: +44(1223)336033, e-mail: deposit@ccdc.cam.ac.uk.
35a Magnus NA.
Confalone PN.
Storace L.
Tetrahedron Lett.
2000,
41:
3015
35b Davies SG.
Fenwick DR.
Ichihara O.
Tetrahedron: Asymmetry
1997,
8:
3387
35c Semple JE.
Wang PC.
Lysenko Z.
Joullié MM.
J. Am. Chem. Soc.
1980,
102:
7505
36a Garcia M.
Azerad R.
Tetrahedron: Asymmetry
1997,
8:
85
36b Ingold CK.
Sako S.
Thorpe JF.
J. Chem. Soc.
1922,
121:
1177
37 Aitken DJ.
Gauzy C.
Pereira E.
Tetrahedron Lett.
2004,
45:
2359
38 Davies SG.
Ichihara O.
Lenoir I.
Walters IAS.
J. Chem. Soc., Perkin Trans. 1
1994,
1411
39 Sabbioni G.
Jones JB.
J. Org. Chem.
1987,
52:
4565
40 Malik V.
Singh P.
Kumar S.
Tetrahedron
2005,
61:
4009
