Regioselective Gold-Catalyzed Allylative Ring Opening of 1,4-Epoxy-1,4-dihydronaphthalenes

Abstract

In the presence of a gold catalyst, the ring opening of 1,4-epoxy-1,4-dihydronaphthalenes with allyltrimethylsilane affords allylnaphthalenes in high yield. For unsymmetrical substrates, high regioselectivity is observed in many cases. This reaction might proceed via tricyclic tetrahydrofuran intermediates which are formed stereoselectively.

allylation - ring opening - regioselectivity - naphthalene - gold catalyst

References and Notes

1 Caple R. Chen GM.-S. Nelson JD. J. Org. Chem.  1971,  36:  2874 

2 Review: Lautens M. Fagnou K. Hiebert S. Acc. Chem. Res.  2003,  36:  48 

3 Nakamura M. Matsuo K. Inoue T. Nakamura E. Org. Lett.  2003,  5:  1373 

4a Bertozzi F. Pineschi M. Macchia F. Arnold LA. Minnaard AJ. Feringa BL. Org. Lett.  2002,  4:  2703 

4b Arrayás RG. Cabrera S. Carretero JC. Org. Lett.  2003,  5:  1333 

4c Arrayás RG. Cabrera S. Carretero JC. Synthesis  2006,  1205 

4d Zhang W. Wang L.-X. Shi W.-J. Zhou Q.-L. J. Org. Chem.  2005,  70:  3734 

4e Millet R. Bernardez T. Palais L. Alexakis A. Tetrahedron Lett.  2009,  50:  3474 

4f Millet R. Gremaud L. Bernardez T. Palais L. Alexakis A. Synthesis  2009,  2101 

For selected references, see:

5a Duan J.-P. Cheng C.-H. Organometallics  1995,  14:  1608 

5b Fugami K. Hagiwara S. Oda H. Kosugi M. Synlett  1998,  477 

5c Lautens M. Renaud J.-L. Hiebert S. J. Am. Chem. Soc.  2000,  122:  1804 

5d Lautens M. Hiebert S. Renaud J.-L. J. Am. Chem. Soc.  2001,  123:  6834 

5e Priego J. Mancheňo OG. Cabrera S. Arrayás RG. Llamas T. Carretero JC. Chem. Commun.  2002,  2512 

5f Lautens M. Hiebert S.
J. Am. Chem. Soc.  2004,  126:  1437 

5g Li M. Yan X.-X. Hong W. Zhu X.-Z. Cao B.-X. Sun J. Hou X.-L. Org. Lett.  2004,  6:  2833 

5h Cabrera S. Arrayás RG. Alonso I. Carretero JC. J. Am. Chem. Soc.  2005,  127:  17938 

5i Imamoto T. Sugita K. Yoshida K. J. Am. Chem. Soc.  2005,  127:  11934 

5j Chen C.-L. Martin SF. J. Org. Chem.  2006,  71:  4810 

5k Zhang T.-K. Yuan K. Hou X.-L. J. Organomet. Chem.  2007,  692:  1912 

5l Imamoto T. Kumada A. Yoshida K. Chem. Lett.  2007,  36:  500 

5m Imamoto T. Saitoh Y. Koide A. Ogura T. Yoshida K. Angew. Chem. Int. Ed.  2007,  46:  8636 

6a Lautens M. Fagnou K. J. Am. Chem. Soc.  2001,  123:  7170 

6b Murakami M. Igawa H. Chem. Commun.  2002,  390 

6c Lautens M. Dockendorff C. Fagnou K. Malicki A. Org. Lett.  2002,  4:  1311 

6d Lautens M. Schmid GA. Chau A. J. Org. Chem.  2002,  67:  8043 

6e Lautens M. Fagnou K. Yang D. J. Am. Chem. Soc.  2003,  125:  14884 

7a Feng C.-C. Nandi M. Sambaiah T. Cheng C.-H.
J. Org. Chem.  1999,  64:  3538 

7b Rayabarapu DK. Chiou C.-F. Cheng C.-H. Org. Lett.  2002,  4:  1679 

7c Wu M.-S. Rayabarapu DK. Cheng C.-H. J. Org. Chem.  2004,  69:  8407 

7d Wu M.-S. Jeganmohan M. Cheng C.-H. J. Org. Chem.  2005,  70:  9545 

8a Wittig G. Pohmer L. Chem. Ber.  1956,  89:  1334 

8b Wolthuis E. Bossenbroek B. DeWall G. Geels E. Leegwater A. J. Org. Chem.  1963,  28:  148 

8c Fetizon M. Anh NT. Bull. Soc. Chim. Fr.  1965,  3208 

8d Cooke MD. Dransfield TA. Vernon JM. J. Chem. Soc., Perkin Trans. 2  1984,  1377 

9 Sawama Y. Sawama Y. Krause N. Org. Lett.  2009,  11:  5034 

10 Deutsch C. Gockel B. Hoffmann-Röder A. Krause N. Synlett  2007,  1790 

Epimerization reports by other groups:

11a Epimerization/rearrangement of alkynyl and aryl C-glycosides with AuCl3: Yeager AR. Min GK. Porco JA. Schaus SE. Org. Lett.  2006,  8:  5065 

11b Epimerization of a 2,5-dihydrofuran during the gold-catalyzed cycloisomerization of an allen-amide: Hyland CJT. Hegedus LS. J. Org. Chem.  2006,  71:  8658 

12 Gold-catalyzed bisallylation of oxabicyclic benzene derivatives: Hsu Y.-C. Datta S. Ting C.-M. Liu R.-S. Org. Lett.  2008,  10:  521 

13

For a two-step synthesis of 2-alkyl-1-naphthols by Pd-catalyzed ring opening of 1,4-epoxy-1,4-dihydro-naphthalenes and subsequent oxidation, see ref. 5j.

14

General Procedure for the Allylative Ring Opening to Synthesize 3d-m
Procedure A
To a solution of the substrate (0.2 mmol) in CH₂Cl₂ (2 mL) were added allylTMS (0.8 mmol) and AuCl₃ (0.01 mmol) at -40 ˚C under nitrogen. After being stirred until reaction was completed, the reaction mixture was concentrated under vacuum. The residue was purified by column chromatog-raphy using hexane-EtOAc (50:1) to give the pure allylation product.
Procedure B
To a solution of the substrate (0.2 mmol) in CH₂Cl₂ (2 mL) were added allylTMS (0.8 mmol), AgSbF₆ (0.03 mmol), and AuCl₃ (0.01 mmol) at -40 ˚C under nitrogen. After being stirred until reaction was completed, the reaction mixture was concentrated under vacuum. The residue was purified by column chromatography using hexane-EtOAc (50:1) to give the pure allylation product.

15 For the synthesis of 2,4-dimethyl-1-naphthols by methyl migration from C-1 to C-2 via ring opening of 1,4-dimethyl-1,4-epoxy-1,4-dihydronaphthalenes, see ref. 8b,c and: Peng F. Fan B. Shao Z. Pu X. Li P. Zhang H. Synthesis  2008,  3043 

16

The determination of relative configuration of 5d,j was accomplished with NOE experiments.

Synthesis of 1-naphthols by regioselective acid-catalyzed ring opening of unsymmetrical substrates:

17a Giles RGF. Hughes AB. Sargent MV. J. Chem. Soc., Perkin Trans. 1  1991,  1581 

17b Batt DG. Jones DG. Greca SL. J. Org. Chem.  1991,  56:  6704 

17c Schlosser M. Castagnetti E. Eur. J. Org. Chem.  2001,  3991 

17d Masson E. Schlosser M. Eur. J. Org. Chem.  2005,  4401 

17e Bailly F. Cottet F. Schlosser M. Synthesis  2005,  791 

18

Regioselective synthesis of 2-alkylated-1,2-dihydro-1-naphthols from unsymmetrical substrates could be only accomplished with Rh catalysts, see ref. 6d.

19

Regiochemistry of 3e-m was determined by NOE experiments.

20

In this paper, the same expressions as in ref. 4c are used. The position of R^¹ in substrates 1e-k is termed distal in relation to the dihydrofuran moiety. The position of R^² is termed proximal.

21

The relative configuration of 5l could not be assigned.

22

Reaction of 1d with crotyltrimethylsilane afforded 1,4-dimethyl-2-(1-methylallyl)naphthalene with 38% yield, which indicates that the allyl nucleophile directly attacks at C-2 of A. The formation of 3 by allylation at C-4 and subsequent Cope rearrangement is disfavored by the steric hindrance at C-4, and the high activation barrier for the Cope rearrangement of 1,5-dienes which usually requires strong heating.

Examples for the trapping of β-silyl cations to give cycloadducts:

23a Nishitani K. Harada Y. Nakamura Y. Yokoo K. Yamakawa K. Tetrahedron Lett.  1994,  35:  7809 

23b Sugita Y. Kimura Y. Yokoe I. Tetrahedron Lett.  1999,  40:  5877