C(1)-substituted menthol derivatives: Self-removing chiral auxiliaries for asymmetric conjugate additions to cycloalkenones

Tetrahedron Letters

Volumn 40, Issue 6, 1999, Pages 1073-1074

  Funk, Raymond L ^a   Yang, Ge ^a  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOALKENE; CYCLOALKENONE DERIVATIVE; MENTHOL; MENTHONE; REAGENT; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHIRALITY; CONJUGATION; HYDROLYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033524690     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02627-6     Document Type: Article

References (20)

1. 1. For an excellent review, see: Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92, 771.
2. 2. For a recent improvement, see: Tomioka, K.; Kanai, M. Tetrahedron Lett. 1995, 36, 4275.
3. 3. (a) Posner, G. H. Acc. Chem. Res. 1987, 20, 72.
4. (b) For the asymmetric conjugate additions to 2-[[-2′-[(methoxymethoxy)methyl]pyrrolidinyl]carbonyl]cyclohex-2-en-l-one, see: Schultz, A. G.; Harrington, R. E. J. Am. Chem. Soc. 1991, 113, 4926.
5. 4. For the related asymmetric synthesis of 3-alkyl-2-methylenecyclohexanones via conjugate addition of cuprates followed by elimination of a pyrrolidine chiral auxiliary, see: Tamura, R.; Watabe, K.-I.; Katayama, H.; Suzuki, H.; Yamamoto, Y. J. Org. Chem. 1990, 55, 408.
6. 5. For the relatively rare attachment of carbon nucleophiles to menthone and subsequent asymmetric transformations, see: (a) Johnson, C. R.; Stark, C. J. Tetrahedron Lett. 1979, 20, 4713.
7. (b) Hart, D. J.; Chillous. S. E.; Hutchinson, D. K. J. Org. Chem. 1982, 47, 5420.
8. (c) Masamune, S.; Parmee, E. R.; Tempkin, O. J. Am. Chem. Soc. 1991, 113, 9365.
9. (d) Masamune, S.; Parmee, E. R. Hong, Y.; Tempkin, O. Tetrahedron Lett. 1992, 33, 1729.
10. (e) Dinesh, C. U.; Kumar, P.; Reddy, R.; Pandey, B.; Puranik, V. G. Tetrahedron:Asymm. 1995, 6, 2961.
11. For a review of asymmetric synthesis using ketal derivatives of menthone, see: (f) Harada, T.; Oku, A. Synlett 1994, 95.
12. For related dioxinone derivatives, see: (g) Demuth, M.; Palomer, A.; Sluma, H.-D.; Kruger, C.; Tsay, Y.-H. Angew. Chem. Int. Ed. Engl.; 1986, 25, 1117.
13. (h) Sato, M.; Abe, Y.; Takayama, K; Sekiguchi, K. Kaneko, C. Inoue, N. Furuya, T. Inukai, N. J. Hetereocyclic Chem 1991, 28, 241.
14. For dioxolanone derivatives, see: (i) Pearson, W. H.; Cheng, M.-C. J. Org. Chem. 1986, 51, 3746. For a benzoxazinone derivative, see: Seki, M.; Yamanaka, T.; Miyake, T.; Ohmizu, H. Tetrahedron Lett. 1996, 37, 5565. For a cyclic nitrone derivative, see: Katagire, N. Okada, M.; Kaneko, C; Furuya, T. Ibid. 1996, 37, 1801.
15. For dioxolanonederivatives, see: (i) Pearson, W. H.; Cheng, M.-C. J. Org. Chem. 1986, 51, 3746. For a benzoxazinone derivative, see: Seki, M.; Yamanaka, T.; Miyake, T.; Ohmizu, H. Tetrahedron Lett. 1996, 37, 5565. For a cyclic nitrone derivative, see: Katagire, N. Okada, M.; Kaneko, C; Furuya, T. Ibid. 1996, 37, 1801.
16. For dioxolanonederivatives, see: (i) Pearson, W. H.; Cheng, M.-C. J. Org. Chem. 1986, 51, 3746. For a benzoxazinone derivative, see: Seki, M.; Yamanaka, T.; Miyake, T.; Ohmizu, H. Tetrahedron Lett. 1996, 37, 5565. For a cyclic nitrone derivative, see: Katagire, N. Okada, M.; Kaneko, C; Furuya, T. Ibid. 1996, 37, 1801.
17. 6. Smith, A. B. III; Branca, S. J.; Guaciaro, M. A.; Korn, A. Org. Syn. 1983, 61, 65.
18. 7. For other examples of highly stereoselective additions of organometallic reagents to menthone, see: (a) Phillippe, J.; Capmau, M.-L.; Chodkiewicz, W. Bull. Soc. Chim., Fr. 1971, 2248.
19. (b) Watanabe, S; Suga, K.; Suematsu, Y.; Suzuki, T. Aust. J. Chem. 1968, 21, 531 and reference 5b.
20. 2,3b The enantiomeric excesses were determined by gas chromatography on a Supelco α-dex 120 column (30 m, .25 mm ID). We thank Professor Xumu Zhang for the use of his instrument.