3-Bromo-propenyl acetate in organic synthesis: An expeditious route to 3-alkyl-4-acetoxy-5-iodomethyl isoxazolidines

Tetrahedron Letters

Volumn 46, Issue 22, 2005, Pages 3789-3792

  Lombardo, Marco ^a   Rispoli, Gabriele ^a   Licciulli, Sebastiano ^a   Trombini, Claudio ^a   Dhavale, Dilip D ^b  

^a UNIVERSITY OF BOLOGNA   (Italy)

^b UNIVERSITY OF PUNE   (India)

Author keywords

4 Acetoxy 5 iodomethyl isoxazolidines; Iodocyclization; Nitrones; Trimethylsilyl triflate; Hydroxyallylation

Indexed keywords

3 BROMOPROPENYLACETATE; ACETIC ACID DERIVATIVE; AMINE; ISOXAZOLIDINE DERIVATIVE; METAL; NITRONE; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG; ZINC;

ALLYLATION; ARTICLE; CHEMICAL REACTION; CYCLIZATION; MATERIALS; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 18144383167     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.04.004     Document Type: Article

References (20)

1. R.C.F. Jones, and J.N. Martin Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry toward Heterocycles and Natural Products Nitrones. Chemistry of Heterocyclic Compounds Vol. 59 2002 Chichester United Kingdom 1 81
2. S. Kanemasa Synlett 2002 1371
3. K.V. Gothelf, and K.A. Jorgensen Chem. Commun. 2000 1449
4. K.V. Gothelf, and K.A. Jorgensen Chem. Rev. 98 1998 863
5. C. Camiletti, D.D. Dhavale, L. Gentilucci, and C. Trombini J. Chem. Soc., Perkin Trans. 1 1993 3157
6. M. Lombardo, S. Licciulli, S. Morganti, and C. Trombini Chem. Commun. 2003 1762
7. M. Lombardo, S. Morganti, M. Tozzi, and C. Trombini Eur. J. Org. Chem. 2002 2823
8. M. Lombardo, and C. Trombini Curr. Org. Chem. 6 2002 1
9. P. Merino, F. Santiago, F.L. Merchan, and T. Tejero Synlett 2000 442
10. M. Lombardo, and C. Trombini Synthesis 2000 759
11. A. Fiumana, M. Lombardo, and C. Trombini J. Org. Chem. 62 1997 5623
12. F. Mancini, M.G. Piazza, and C. Trombini J. Org. Chem. 56 1991 4246
13. M. Lombardo, S. Spada, and C. Trombini Eur. J. Org. Chem. 1998 2361
14. M. Lombardo, S. Licciulli, and C. Trombini Pure Appl. Chem. 76 2004 657
15. 5a,5b,5c
16. Recently, Petrini et al. studied the reaction of 11 with imines produced in situ from α-amidoalkyl phenylsulfones, and reported an appreciable anti-diastereoselectivity: see M. Petrini, R. Profeta, and P. Righi J. Org. Chem. 67 2002 4530 Conversely, the addition of 11 to aldehydes, both in aqueous and in polar aprotic solvents, is characterized by a unique dependence of diastereoselectivity upon the nature of the aldehyde. While saturated aldehydes afford anti adducts, conjugated and aromatic aldehydes give syn adducts (Ref. 8)
17. 2 (3 × 5 mL). O-TMS hydroxylamines 13 are obtained almost pure by flash-chromatography purification on silica gel (cyclohexane/ethyl acetate 7:3); to avoid desilylation the elution should be as fast as possible
18. 3 (3 x 5 mL). Isoxazolidines 14 were separated by flash-chromatography eluting with cyclohexane/ethyl acetate 98:2
19. O-TMS hydroxylamines 13e and f were recovered almost unchanged from the iodocyclization reaction mixture
20. Typical NOE enhancements: