Palladium(0)/indium iodide-mediated allylations of electrophiles generated from the hydrolysis of Eschenmoser's salt: one-pot preparation of diverse carbocyclic scaffolds

Tetrahedron Letters

Volumn 51, Issue 23, 2010, Pages 3050-3052

  Cesario, Cara ^a   Miller, Marvin J ^a  

^a UNIVERSITY OF NOTRE DAME   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; ALCOHOL DERIVATIVE; ALLYL ACETIC ACID; ALLYLINDIUM; CARBOCYCLIC NUCLEOSIDE; CYCLOPENTENE DERIVATIVE; ELECTROPHILE; ESCHENMOSER SALT; FORMALDEHYDE; HYDROXYL GROUP; INDIUM; INDIUM IODIDE; METAL DERIVATIVE; NITROSO DERIVATIVE; PALLADIUM COMPLEX; SODIUM CHLORIDE; TETRAHYDROFURAN; UNCLASSIFIED DRUG;

ALLYLATION; AQUEOUS SOLUTION; ARTICLE; CHIRALITY; DIASTEREOISOMER; DIELS ALDER REACTION; ENANTIOSELECTIVITY; HYDROLYSIS; ONE POT SYNTHESIS; STEREOCHEMISTRY; SUBSTITUTION REACTION;

ALNUS;

EID: 77953119663     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.04.007     Document Type: Article

References (32)

1. Okachi T., Fujimoto K., and Onaka M. Org. Lett. 4 (2002) 1667-1669
2. Harayama H., Kimura M., Tanaka S., and Tamaru Y. Tetrahedron Lett. 39 (1998) 8475-8478
3. Martin R.J.L. Aust. J. Chem. 7 (1954) 400-405 and references therein
4. Snider B.B., Rodini D.J., Kirk T.C., and Cordova R. J. Am. Chem. Soc. 104 (1982) 555-563
5. Maruoka K., Concepcion A.B., Hirayama N., and Yamamoto H. J. Am. Chem. Soc. 112 (1990) 7422-7423
6. Ogawa C., and Kobayashi S. Chem. Lett. 36 (2007) 56-57
7. Kobayashi S. Chem. Lett. 20 (1991) 2187-2190
8. For a review of synthetic routes to cyclopentyl carbocyclic nucleosides, see:. Crimmins M.T. Tetrahedron 54 (1998) 9229-9272
9. For a review of synthetic routes to carbasugars, see:. Arjona O., Gomez A.M., Lopez J.C., and Plumet J. Chem. Rev. 107 (2007) 1919-2036
10. Jung M.E., and Hakjune R. J. Org. Chem. 59 (1994) 4719-4720
11. Daluge S., and Vince R. J. Org. Chem. 43 (1978) 2311-2320
12. Griffiths G.J., and Previdoli F.E. J. Org. Chem. 58 (1993) 6129-6131
13. Jagt J.C., and Van Leusen A.M. J. Org. Chem. 39 (1974) 564-566
14. In the synthesis of BXC-1812, see:. Mineno T., and Miller M.J. J. Org. Chem. 68 (2003) 6591-6596
15. In the synthesis of carbovir, see:. Peel M.R., Sternbach D.D., and Johnson M.R. J. Org. Chem. 56 (1991) 4990-4993
16. In the synthesis of (-)-carbovir, (-)-aristeromycin, (-)-neplanocin A and related compounds, see:. Trost B.M., Madsen R., Guile S.D., and Brown B. J. Am. Chem. Soc. 122 (2000) 5947-5956 and references therein
17. For the synthesis of 1a, see:. McGuigan C., Hassan-Abdallah A., Srinivasan S., Wang Y., Siddiqui A., Daluge S.M., Gudmundsson K.S., Zhou H., McLean E.W., Peckham J.P., Burnette T.C., Marr H., Hazen R., Condreay L.D., Johnson L., and Balzarini J. J. Med. Chem. 49 (2006) 7215-7226
18. Daluge S.M., Martin M.T., Sickles B.R., and Livingston D.A. Nucleosides Nucleotides Nucleic Acids 19 (2000) 297-327
19. Vince R., and Hua M. J. Med. Chem. 33 (1990) 17-21
20. For the synthesis of 1b, see:. Grumann A., Marley H., and Taylor R.J.K. Tetrahedron Lett. 36 (1995) 7767-7768
21. For reviews:. Araki S., and Hirashita T. In: Crabtree R.H., and Mignos D.M.P. (Eds). Comprehensive Organometallic Chemistry III Vol. 9 (2007), Elsevier, Oxford Chapter 9.14
22. Podlech J., and Maier T.C. Synthesis 5 (2003) 633-655
23. Cesario C., and Miller M.J. Org. Lett. 11 (2009) 1293-1295
24. Lee W., Kim K.H., Surman M.D., and Miller M.J. J. Org. Chem. 68 (2003) 139-149
25. Electrochemical indium-catalyzed allylations of esters have been achieved, see:. Hilt G., and Smolko K.I. Angew. Chem., Int. Ed. 40 (2001) 3399-3402
26. Allylindium(III) species, prepared from allylhalide and indium metal in DMF, is unreactive towards esters and cyano groups, see:. Araki S., Ito H., and Butsuga Y. J. Org. Chem. 53 (1988) 1833-1835
27. Indium-mediated allylations of aldamines have been achieved, see:. Vilaivan T., Winotapan C., Shinada T., and Ohfune Y. Tetrahedron Lett. 42 (2001) 9073-9076
28. In contrast to our observations, zinc-mediated allylations of iminium electrophiles (generated in situ from formaldehyde and amine in water) provide homoallylic amine products, see:. Estevam I.H.S., and Bieber L.W. Tetrahedron Lett. 44 (2003) 667-670
29. Compound 7d has been synthesized by using Pd(0)/InI allylation with cycloadduct 2b in the presence of Eschenmoser's salt under anhydrous conditions, see Ref. 15a.
30. Cesario C., Tardibono L.P., and Miller M.J. J. Org. Chem. 74 (2009) 448-451
31. Allyl acetate (-)-8 is available from kinetic enzymatic resolution with Candida antarctica B lipase. See:. Mulvihill M.J., Gage J.L., and Miller M.J. J. Org. Chem. 63 (1998) 3357-3363
32. Cesario, C.; Tardibono, L. P.; Miller, M. J. Tetrahedron Lett., in press.