Diastereocontrol in the Synthesis of 2,3,4-Trisubstituted Pyrrolidines and Tetrahydrofurans via a Palladium(II)-Catalyzed Three-Component Coupling Reaction

Sandeep Raikar; Benoy Kumar Pal; Helena C. Malinakova

doi:10.1055/s-0031-1290969

Synthesis, Table of Contents

Synthesis 2012; 44(13): 1983-1992
DOI: 10.1055/s-0031-1290969

paper

Diastereocontrol in the Synthesis of 2,3,4-Trisubstituted Pyrrolidines and Tetrahydrofurans via a Palladium(II)-Catalyzed Three-Component Coupling Reaction

Sandeep Raikar

Department of Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, KS 66045, USA

Center of Excellence in Chemical Methodologies and Library Development, University of Kansas, 2034 Becker Drive, Shankel Structural Biology Center, West Campus, Lawrence, KS 66047, USA, Fax: +1(785)8645396 Email: hmalina@ku.edu

,

Benoy Kumar Pal

Department of Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, KS 66045, USA

Center of Excellence in Chemical Methodologies and Library Development, University of Kansas, 2034 Becker Drive, Shankel Structural Biology Center, West Campus, Lawrence, KS 66047, USA, Fax: +1(785)8645396 Email: hmalina@ku.edu

,

Helena C. Malinakova*

Department of Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, KS 66045, USA

Center of Excellence in Chemical Methodologies and Library Development, University of Kansas, 2034 Becker Drive, Shankel Structural Biology Center, West Campus, Lawrence, KS 66047, USA, Fax: +1(785)8645396 Email: hmalina@ku.edu

› Author Affiliations

Abstract

All articles of this category

Abstract

The synthesis of trisubstituted pyrrolidines and tetrahydrofurans from boronic acids, allenes, and imines or aldehydes via a five- and a three-step protocol, respectively, is described. The assignment of the relative stereochemistry in the pyrrolidines and tetrahydrofurans confirmed the mechanistically significant stereochemical divergence of the palladium-catalyzed three-component coupling reaction. The methodology is applicable to the preparation of combinatorial libraries of pyrrolidines related to pharmaceutical agents and bioactive natural products.

Key words

stereoselective synthesis - heterocycles - palladium - multicomponent reactions - ring closure

Full Text

References

References

1a Jae H.-S, Winn M, von Geldern TW, Sorensen BK, Chiou WJ, Nguyen B, Marsh KC, Opgenorth TJ. J. Med. Chem. 2001; 44: 3978
1b Yang B.-H, Zhang W.-D, Liu R.-H, Li T.-Z, Zhang C, Zhou Y, Su J. J. Nat. Prod. 2005; 68: 1175
1c Lin SL, Liu X.-H, Shen Y.-H, Li H.-L, Shan L, Liu R.-H, Xu X.-K, Zhang W.-D, Wang H. J. Nat. Prod. 2010; 73: 632

2 Slater MJ, Amphlett EM, Andrews DM, Bravi G, Burton G, Cheasty AG, Corfield JA, Ellis MR, Fenwick RH, Fernandes S, Guidetti R, Haigh D, Hartley CD, Howes PD, Jackson DL, Jarvest RL, Lovegrove VL. H, Medhurst KJ, Parry NR, Price H, Shah P, Singh OM. P, Stocker R, Thommes P, Wilkinson C, Wonacott A. J. Med. Chem. 2007; 50: 897
3 Baldwin JE, Fryer AM, Pritchard GJ. J. Org. Chem. 2001; 66: 2588

4a Chen C, Li X, Schreiber SL. J. Am. Chem. Soc. 2003; 125: 10174
4b Scott ME, Han W, Lautens M. Org. Lett. 2004; 6: 3309
4c Pohlhaus PD, Sanders SD, Parsons AT, Li W, Johnson JS. J. Am. Chem. Soc. 2008; 130: 8642
4d Chaulagain MR, Aron ZD. J. Org. Chem. 2010; 75: 8271

5 Barker G, McGrath JL, Klapars A, Stead A, Stead D, Zhou G, Campos KR, O’Brien P. J. Org. Chem. 2011; 76: 5936

6a Bueno ND, Jimenez A, Pedregal C, Vidal P. Tetrahedron Lett. 2006; 17: 2489
6b Yazici A, Pyne SG. Synthesis 2009; 513
6c Peixoto S, Nguyen TM, Crich D, Delpech B, Marazano C. Org. Lett. 2010; 12: 4760

7a Paderes MC, Chemler SR. Org. Lett. 2009; 11: 1915
7b Komsta Z, Barbasiewicz M, Makosza M. J. Org. Chem. 2010; 75: 3251
7c Zhou L, Chen J, Tan CK, Yeung Y.-Y. J. Am. Chem. Soc. 2011; 133: 9164
7d Kotland A, Accadbled F, Robeyns K, Behr J.-B. J. Org. Chem. 2011; 76: 4094

8a Hopkins CD, Malinakova HC. Org. Lett. 2006; 8: 5971
8b Hopkins CD, Malinakova HC. Synthesis 2007; 3558

9 Hopkins CD, Malinakova HC. Org. Lett. 2004; 6: 2221

10a Murphy MM, Schullek JR, Gordon EM, Gallop MA. J. Am. Chem. Soc. 1995; 117: 7029
10b Kumar A, Gupta G, Srivastava S. J. Comb. Chem. 2010; 12: 458
10c Liu H, Dou G, Shi D. J. Comb. Chem. 2010; 12: 292

11a An H, Cook PD. Chem. Rev. 2000; 100: 3311
11b Sunderhaus JD, Martin SF. Chem.–Eur. J. 2009; 15: 1300
11c Ganem B. Acc. Chem. Res. 2009; 42: 463
11d See also ref. 4d

12 Hopkins CD. Ph.D. Thesis. The University of Kansas; USA: 2007
13 Verkade JM. M, van Hemert LJ. C, Quaedflieg PJ. L. M, Alsters PL, van Delft FL, Rutjes FP. J. T. Tetrahedron Lett. 2006; 47: 8109

14a Kronenthal DR, Han CY, Taylor MK. J. Org. Chem. 1982; 47: 2765
14b Hasegawa M, Taniyama D, Tomioka K. Tetrahedron 2000; 56: 10153
14c Overman LE, Owen CE, Pavan MM. Org. Lett. 2003; 5: 1809
14d Hata S, Iguchi M, Iwasawa T, Yamada K.-I, Tomioka K. Org. Lett. 2004; 6: 1721
14e Marin SD. L, Martens T, Mioskowski C, Royer J. J. Org. Chem. 2005; 70: 10592

15a Maligres PE, Waters MM, Lee J, Reamer RA, Askin D, Ashwood MS, Cameron M. J. Org. Chem. 2002; 67: 1093
15b Sajjadi Z, Lubell WD. J. Pept. Res. 2005; 65: 298

16 Burkhardt ER, Matos K. Chem. Rev. 2006; 106: 2617
17 Bieber LW, de Araujo MC. F. Molecules 2002; 7: 902
18 Lucas BS, Luther LM, Burke SD. Org. Lett. 2004; 6: 2965
19 Rujirawanich J, Gallagher T. Org. Lett. 2009; 11: 5494
20 Prakash GK. S, Do C, Wang F, Mathew T, Olah GA. Synthesis 2010; 1891

21a Still WC, Barrish JC. J. Am. Chem. Soc. 1983; 105: 2487
21b Loiseleur O, Koch G, Wagner T. Org. Process Res. Dev. 2004; 8: 597

22a Houk KN, Rondan NG, Wu YD, Metz JT, Paddon-Row MN. Tetrahedron 1984; 40: 2257
22b Hoffmann RW. Chem. Rev. 1989; 89: 1841

23 Evans DA, Ratz AM, Huff BE, Sheppard GS. J. Am. Chem. Soc. 1995; 117: 3448
24 X-ray crystallographic data were deposited at the Cambridge Crystallographic Data Centre, CCDC number 858605

Supplementary Material

Supporting Information