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Synthesis 2003(18): 2805-2810
DOI: 10.1055/s-2003-42457
DOI: 10.1055/s-2003-42457
PAPER
© Georg Thieme Verlag Stuttgart · New York
Enantioselective Syntheses of (-)-(R)-Rolipram, (-)-(R)-Baclofen and Other GABA Analogues via Rhodium-Catalyzed Conjugate Addition of Arylboronic Acids
Further Information
Received
20 August 2003
Publication Date:
04 November 2003 (online)
Publication History
Publication Date:
04 November 2003 (online)
Abstract
Highly enantioselective syntheses of two important γ-aminobutyric acid (GABA) analogues, the antispastic drug (-)-(R)-Baclofen and the antidepressant agent (-)-(R)-Rolipram, are reported. Key-steps in both syntheses are the Rh-catalyzed asymmetric 1,4-additions of arylboronic acids to 4-aminobut-2,3-enoic acid derivatives.
Key words
asymmetric synthesis - catalysis - conjugate addition - rhodium - arylboronic acid
-
1a
Mann A.Boulanger T.Brandau B.Durant F.Evrard G.Heaulme M.Desaulles E.Wermuth C.-G. J. Med. Chem. 1991, 34: 1307 -
1b
Karla R.Ebert B.Thorkildsen C.Herdeis C.Johansen TN.Nielsen B.Krogsgaard-Larsen P. J. Med. Chem. 1999, 42: 2053 - 2
Olpe HR.Demiéville H.Baltzer V.Bencze WL. Eur. J. Pharmacol. 1978, 52: 133 - 3
Diaz A.Siro JG.García-Navío JL.Vaquero JJ.Alvarez-Builla J. Synthesis 1997, 559 -
4a
Herdeis C.Hubmann HP. Tetrahedron: Asymmetry 1992, 3: 1213 -
4b
Langlois N.Dahuron N.Wang H.-S. Tetrahedron 1996, 52: 15117 -
4c
Licandro E.Maiorana S.Baldoli C.Capella L.Perdicchia D. Tetrahedron: Asymmetry 2000, 11: 975 -
4d
Schoenfelder A.Mann A.Le Coz S. Synlett 1993, 63 -
4e
Thakur VV.Nikalje MD.Sudalai A. Tetrahedron: Asymmetry 2003, 14: 581 -
4f
Corey EJ.Zhang F.-Y. Org. Lett. 2000, 2: 4257 -
4g
Anada M.Hashimoto S.-I. Tetrahedron Lett. 1998, 39: 79 -
4h
Resende P.Almeida WP.Coelho F. Tetrahedron: Asymmetry 1999, 10: 2113 -
4i
Wang M.-X.Zhao S.-M. Tetrahedron Lett. 2002, 43: 6617 -
4j
Brenna E.Caraccia N.Fuganti C.Fuganti D.Grasseli P. Tetrahedron: Asymmetry 1997, 8: 3801 -
4k
Belda O.Lundgren S.Moberg C. Org. Lett. 2003, 5: 2275 -
5a
Yoon CH.Nagle A.Chen C.Gandhi D.Jung KW. Org. Lett. 2003, 5: 2259 -
5b
Braun M.Opdenbusch K.Unger C. Synlett 1995, 1174 -
5c
Meyers AI.Snyder L. J. Org. Chem. 1993, 58: 36 -
5d
Mulzer J.Zuhse R.Schmiechen R. Angew. Chem. 1992, 104: 914 -
5e
Barluenga J.Fernández-Rodríguez MA.Aguilar E.Fernández-Marí F.Salinas A.Olano B. Chem. Eur. J. 2001, 7: 3533 -
5f
Anada M.Mita O.Watanabe H.Kitagaki S.Hashimoto S. Synlett 1999, 11: 1775 - 6 For a preliminary report on part of the work described here, see:
Meyer O.Becht J.-M.Helmchen G. Synlett 2003, 1539 - 7
Sakai M.Hayashi H.Miyaura N. Organometallics 1997, 16: 4229 -
8a
Takaya Y.Ogasawara M.Hayashi T.Sakai M.Miyaura N. J. Am. Chem. Soc. 1998, 120: 5579 -
8b
Takaya Y.Senda T.Kurushima H.Ogasawara M.Hayashi T. Tetrahedron: Asymmetry 1999, 10: 4047 -
8c
Fagnou K.Lautens M. Chem. Rev. 2003, 103: 169 - 9
De Vita RJ.Frontier AJ.Schoen WR.Wyvratt MJ.Fisher MH.Cheng K.Chan WW.-S.Butler BS.Smith RG. Helv. Chim. Acta 1997, 80: 1244 -
10a
Frigerio M.Santagostino M.Sputore S. J. Org. Chem. 1999, 64: 4537 -
10b
More JD.Finney NS. Org. Lett. 2002, 4: 3001 -
10c
Chhabra SR.Mahajan A.Chan WC. J. Org. Chem. 2002, 67: 4017 -
10d
Àlvarez M.Fernández D.Joule JA. Tetrahedron Lett. 2001, 42: 315 -
11a
Sakuma S.Sakai M.Itooka R.Miyaura N. J. Org. Chem. 2000, 65: 5951 -
11b
Itooka R.Iguchi Y.Miyaura N. J. Org. Chem. 2003, 68: 6000 - 12
Ishiyama T.Murata M.Miyaura N. J. Org. Chem. 1995, 60: 7508 - 13
Falck JR.Bondlela M.Venkataraman SK.Srinivas D. J. Org. Chem. 2001, 66: 7148 - 14
Langlois N.Wang H.-S. Synth. Commun. 1997, 27: 3133 - 15
Lintunen T.Yli-Kauhaluoma JT. Bioorg. Med. Chem. Lett. 2000, 15: 1749 - 16
Mattingly PG. Synthesis 1990, 367 - 17 Note added in proof: Using a hydroxorhodium catalyst, generated in situ, recently developed (compound 8 in:
Hayashi T.Takahashi M.Takaya Y.Ogasawara M. J. Am. Chem. Soc. 2002, 124: 5052 ), the reaction of 3a with 6a proceeded at 70 °C (other conditions as in entry 3 of Table 1) within 1 h to give (S)-7a in 70% isolated yield with 95%ee. Accordingly, use of the new catalyst would likely allow an improvement for all reactions described here