[4+2] Cyclization reactions of chiral Cβ-substituted Fischer alkenyl carbene complexes: efficient synthesis of enantiopure cyclohexenone and norbornene derivatives

Tetrahedron

Volumn 63, Issue 28, 2007, Pages 6542-6547

  Barluenga, José ^a   Gómez, Aránzazu ^a   de Prado, Ana ^a   Panday, Narendra ^a   Santamaría, Javier ^a   Tomás, Miguel ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

4+2 Cyclization; Carbene complexes; Chiral pool; Diastereoselectivity

Indexed keywords

2 CYCLOHEXENONE; ALKENYL GROUP; CARBENE; CARBONYL DERIVATIVE; ESTER DERIVATIVE; NORBORNENE DERIVATIVE;

ARTICLE; CHIRALITY; CRYSTAL STRUCTURE; CYCLIZATION; DIASTEREOISOMER; ENANTIOMER; OXIDATION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 34249302078     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.03.038     Document Type: Article

References (32)

1. For recent reviews leading to the formation of carbo and heterocycles form Fischer carbene complexes, see:. Barluenga J., Santamaría J., and Tomás M. Chem. Rev. 104 (2004) 2259
2. Barluenga J., Rodríguez F., Fañanás F.J., and Flórez J. Top. Organomet. Chem. 13 (2004) 59
3. Wulff W.D., Bauta W.E., Kaesler R.W., Lankford P.J., Miller R.A., Murray C.K., and Yang D.C. J. Am. Chem. Soc. 112 (1990) 3642
4. Wulff W.D., and Yang D.C. J. Am. Chem. Soc. 105 (1983) 6726
5. For selected reviews in organic synthesis with Fischer carbene complexes, see:
6. Dörwald F.J. Metal Carbenes in Organic Synthesis (1999), Wiley-VCH, New York, NY
7. de Meijere A., Schirmer H., and Duetsch M. Angew. Chem., Int. Ed. 39 (2000) 3964
8. Herndon J.W. Tetrahedron 56 (2000) 1257
9. Dötz K.H., Jakel C., and Haase W.C. J. Organomet. Chem. 617-618 (2001) 119
10. Herndon J.W. Coord. Chem. Rev. 250 (2006) 1889
11. See Ref 1.
12. Wulff W.D. Organometallics 17 (1998) 3116
13. Powers T.S., Jiang W., Su J., Wulff W.D., Waltermire B.E., and Rheingold A.L. J. Am. Chem. Soc. 119 (1997) 6438
14. Two examples with chiral alkynyl carbene complexes have been reported:
15. Chiral aminoalkynyl carbenes:. Rahm A., Rheingold A.L., and Wulff W.D. Tetrahedron 56 (2000) 4951
16. Chiral alkoxyalkynyl carbenes:. Barluenga J., de la Rúa R.B., de Saa D., Ballesteros A., and Tomás M. Angew. Chem., Int. Ed. 44 (2005) 4981
17. Dötz K.H., Paetsch D., and Le Bozec H. J. Organomet. Chem. 589 (1999) 11
18. Weyershausen B., Nieger M., and Dötz K.H. J. Org. Chem. 64 (1999) 4206
19. Weyershausen B., Nieger M., and Dötz K.H. Organometallics 17 (1998) 1602
20. Barluenga J., Panday N., Santamaría J., de Prado A., and Tomás M. ARKIVOC x (2003) 576
21. Barluenga J., de Prado A., Santamaría J., and Tomás M. Angew. Chem., Int. Ed. 44 (2005) 6583
22. Barluenga J., de Prado A., Santamaría J., and Tomás M. Chem.-Eur. J. 13 (2007) 1326
23. For isolated examples dealing with the cycloaddition of electron-poor alkenes containing the dioxolane chiral auxiliary, see:
24. Ortuño R.M., Ibarzo J., d'Angelo J., Dumas F., Alvarez-Larena A., and Piniella J.F. Tetrahedron: Asymmetry 7 (1996) 127
25. Asano M., Inoue M., Watanabe K., Abe H., and Katoh T. J. Org. Chem. 71 (2006) 6942
26. Alternatively, enantiopure compound 8 is accessible by acid treatment (concd HCl, MeOH, 0 °C) of the diastereomeric mixture of the primary cycloadducts 4a and 4b in 62 and 66% overall yields from carbenes 1a and 1b.
27. Casas R., Parella T., Branchadell V., Oliva A., Ortuño R.M., and Guingant A. Tetrahedron 48 (1992) 2659
28. After the chromatographic purification, cycloadduct 12 was obtained contaminated with traces (<3%) of a non-identified compound.
29. Unlike electron-poor allenes, only the intramolecular version of the [4+2] cycloaddition of electron-rich allenes is known:. Murakami M., and Mitsuda T. In: Krauns N., and Hashmi A.S.K. (Eds). Modern Allene Chemistry Vol. 2 (2004), Wiley-VCH, Weinheim 760-791
30. Barry R.D. Chem. Rev. 64 (1964) 229
31. Houser F.M., and Baghdanov V.M.J. Org. Chem. 53 (1988) 4676
32. Mali R.S., and Babu K.N. J. Org. Chem. 63 (1998) 2488