Stereoselective [2,3]-Wittig rearrangement of (1S,2R)-1-amino-indan-2-ol derived amide enolates

Tetrahedron Letters

Volumn 38, Issue 15, 1997, Pages 2633-2636

  Kress, Michael H ^a   Yang, Chunhua ^a   Yasuda, Nobuyoshi ^a   Grabowski, E J J ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROXYACID;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; GAS CHROMATOGRAPHY; IN VITRO STUDY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030909045     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00438-3     Document Type: Article

References (19)

1. Maligres, P. E.; Weissman, S. A.; Upadhyay, V.; Cianciosi, S. J.; Reamer, R. A.; Purick, R. M.; Sager, J.; Rossen, K.; Eng, K. K.; Askin, D.; Volante, R. P.; Reider, P. J. Tetrahedron 1996, 52, 3327. Davies, I. W.; Senanayake, C. H.; Castonguay, L.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1995, 36, 7619. ibid., 1996, 37, 1725.
2. Maligres, P. E.; Weissman, S. A.; Upadhyay, V.; Cianciosi, S. J.; Reamer, R. A.; Purick, R. M.; Sager, J.; Rossen, K.; Eng, K. K.; Askin, D.; Volante, R. P.; Reider, P. J. Tetrahedron 1996, 52, 3327. Davies, I. W.; Senanayake, C. H.; Castonguay, L.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1995, 36, 7619. ibid., 1996, 37, 1725.
3. Maligres, P. E.; Weissman, S. A.; Upadhyay, V.; Cianciosi, S. J.; Reamer, R. A.; Purick, R. M.; Sager, J.; Rossen, K.; Eng, K. K.; Askin, D.; Volante, R. P.; Reider, P. J. Tetrahedron 1996, 52, 3327. Davies, I. W.; Senanayake, C. H.; Castonguay, L.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1995, 36, 7619. ibid., 1996, 37, 1725.
4. a) Nakai, T.; Mikami, K. Organic Reactions, vol. 46, John Wiley & Sons, Inc.; New York, NY; 1994; pp 105-210.
5. b) For the [2,3]-Wittig rearrangement of oxazolines derived from cis-2-amino-1-acenaphthenol, see: Sudo, A.; Hashimoto, Y.; Kimoto, H.; Hayashi, K.; Saigo, K. Tetrahedron Asym. 1994, 5, 1333.
6. a) Evans, D. A.; Weber, A. E. J. Am. Chem. Soc. 1987, 109, 7151.
7. b) Waid, P. P.; Flynn, G. A.; Huber, E. W.; Sabol, J. S. Tetrahedron Lett. 1996, 37, 4091.
8. 3)].
9. The propensity of α-allyloxy-cis-amino-indanol derived amide enolates to undergo [2,3] rearrangement is a marked difference in reactivity when compared to similar amide enolates containing the Evans oxazolidinone auxiliary (which do not undergo [2,3] rearrangement), see: Nakai, T.; Mikami, K. Chem. Rev. 1986, 86, 885. We attribute this difference to an increase of carbon-based anionic character in the former case.
10. 13C NMR. The absolute stereochemistry of this product was not proven, but is assumed to be (2S, 3R). On a preparative scale this minor product was separated by silica gel chromatography.
11. The [2,3] rearrangements of the zirconium enolates of a variety of trans-2,5-bis-(methoxymethoxymethyl) pyrrolidine amides have been reported to give excellent syn selectivity, with moderate to good isolated yields, see: Uchikawa, M.; Hanamoto, T.; Katsuki, T.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 4577.
12. Diastereomeric ratios of 4E:4T were routinely assayed on a HP 6890 GC with FID, using a splitless injection of a heptane solution onto a 5m HP-1/30m DB-23 joined column (He carrier).
13. 3)] was available by normal phase, preparative HPLC on a YMC-pack CN column. The authors have deposited the coordinates of 4E in the Cambridge Crystallographic Database.
14. 1+ proton of the amino-indanol auxiliary.
15. The absolute stereochemistry of the [2,3]-Wittig rearranged products of amides 5, and 7 were determined after conversion to L-isoleucine and L-norvaline respectively, followed by GC comparison of their trifluoroacetamide methyl esters to authentic samples on a Alltech Chirasil-Val column (25m) as per: Abe, I.; Izumi, K.; Kuramoto, S.; Musha, S. J. High Res. Chromo. Chromo. Comm. 1981, 549.
16. 2
17. Similar low anti selectivity was observed for the [2,3] rearrangement of (cis-2-butenyloxy)-pyrrolidine amide enolates, see footnote 4 of: Mikami, K.; Takahashi, O.; Kasuga, T.; Nakai, T. Chem. Lett. 1985, 1729.
18. Attempts to achieve this transformation in one pot with diphenyl phosphorazidate and DBU lead to significant amounts of the elimination product, see: Thompson, A. S.; Humphrey, G. R.; DeMarco, A. M.; Mathre, D. J., Grabowski, E. J. J. J. Org. Chem. 1993, 58, 5886.
19. 1H NMR. The source of this leak in stereospecificity is currently under investigation.