Enantio- and Diastereoselective [3+2] Cycloadditions of Azomethine Ylides with Ag(I)-Phosphinooxazoline Catalysts

Remo Stohler; Florentine Wahl; Andreas Pfaltz

doi:10.1055/s-2005-865313

PAPER

Enantio- and Diastereoselective [3+2] Cycloadditions of Azomethine Ylides with Ag(I)-Phosphinooxazoline Catalysts

Remo Stohler, Florentine Wahl, Andreas Pfaltz*
Department of Chemistry, University of Basel, St. Johanns-Ring 19, 4056 Basel, Switzerland
e-Mail: andreas.pfaltz@unibas.ch;

Abstract

All articles of this category

Abstract

Chiral Ag(I)-phosphinooxazoline (PHOX) complexes are efficient catalysts for [3+2] cycloadditions of azomethine ylides with α,β-unsaturated carboxylic esters. In intramolecular cycloadditions, virtually complete diastereocontrol and enantiomeric excesses of up to 99% have been observed.

Key words

asymmetric catalysis - Ag(I) complexes - [3+2] cycloaddition - azomethine ylides - phosphinooxazolines

Full Text

References

1 Maclean D. Schullek JR. Murphy MM. Ni Z.-J. Gordon EM. Gallop MA. Proc. Natl. Acad. Sci. U.S.A. 1997, 94: 2805

2a Gong Y.-D. Kim S.-K. Yoo S.-E. Kurth MJ. Bull. Chem. Soc. Jpn. 2002, 75: 2477

2b Snider BB. Ahn Y. Foxman BM. Tetrahedron Lett. 1999, 40: 3339

2c Mallassene R. Sanchez-Bajo L. Toupet L. Hurvois J.-P. Moinet C. Synlett 2002, 1500

2d Ho TCT. Jones K. Tetrahedron 1997, 53: 8287

2e Lovely CJ. Mahmud H. Dias HVR. Tetrahedron 2001, 57: 4095

2f Fejes I. Nyenges M. Töke L. Tetrahedron Lett. 2000, 41: 7951

2g Gu YG. Zhang X. Clark RF. Djuric S. Ma Z. Tetrahedron Lett. 2004, 45: 3051

2h Nakagawa M. Lai Z. Torisawa Y. Hino T. Heterocycles 1990, 31: 999

3a Allway P. Grigg R. Tetrahedron Lett. 1991, 32: 5817

3b Grigg R. Tetrahedron: Asymmetry 1995, 6: 2457

4 Longmire JM. Wang B. Zhang X. J. Am. Chem. Soc. 2002, 124: 13400

5 Gothelf AS. Gothelf KV. Hazell RG. Jørgenson KA. Angew. Chem. Int. Ed. 2002, 41: 4236

6 Chen C. Li S. Schreiber SL. J. Am. Chem. Soc. 2003, 125: 10174

7 Helmchen G. Pfaltz A. Acc. Chem. Res. 2000, 33: 336

For bisoxazoline ligands with two geminal substituents at C(5) see:

8a Denmark SE. Stavenger RA. Faucher A.-M. Edwards JP. J. Org. Chem. 1997, 62: 3375

8b Gupta AD. Bhuniya D. Singh VK. Tetrahedron 1994, 50: 13725

8c Alexander K. Cook S. Gibson CL. Tetrahedron Lett. 2000, 41: 7135

8d Andrus MB. Argade AB. Chen X. Pamment MG. Tetrahedron Lett. 1995, 36: 2945

9 Ciganek E. Synthesis 1995, 1311

10 Ayerbe M. Arrieta A. Cossío FP. J. Org. Chem. 1998, 63: 1795

For analogons of non-enantioselective reactions, see:

11a Grigg R. Duffy LM. Dorrity MJ. Malone JF. Rajviroongit S. Thornton-Pett M. Tetrahedron 1990, 46: 2213

11b Adill H. Grigg R. Sridhanan V. Surendrakumar S. Tetrahedron 1988, 44: 4953

11c Tsuge O. Ueno K. Oe K. Chem. Lett. 1981, 135

11d Grigg R. Donegan G. Gunaratne HQN. Kennedy DA. Malone JF. Sridhanan V. Thianpatanagul S. Tetrahedron 1989, 45: 1723

12 Altomare A. Cascarano G. Giacovazzo G. Guagliardi A. Burla MC. Polidori G. Camalli M. J. Appl. Cryst. 1994, 27: 435

13 Watkin DJ. Prout CK. Carruthers JR. Betteridge PW. Cooper RI. CRYSTALS Issue 11: Chemical Crystallography Laboratory; Oxford: 2001.