Diastereoselective addition of organozinc reagents to 2-alkyl-3- (arylsulfanyl)propanals

Tetrahedron

Volumn 60, Issue 47, 2004, Pages 10659-10669

  Larsson, Michael ^a   Galandrin, Elodie ^a   Högberg, Hans Erik ^a  

^a MID SWEDEN UNIVERSITY   (Sweden)

Author keywords

Chelation; Diastereoselective additions; Dimethylzinc; Pheromones; Titanium tetrachloride

Indexed keywords

2 [(PHENYLSULFANYL)METHYL]DECANAL; 2 [(PHENYLSULFANYL)METHYL]DODECANAL; 2 [(PHENYLSULFANYL)METHYL]PENTANAL; 2 METHYL 3 [(METHYLPHENYL)SULFANYL]PROPANAL; 3 (BUTYLSULFANYL) 2 METHYLPROPANAL; 3 (TERT BUTYLSULFANYL) 2 METHYLPROPANAL; 3 [(2 METHOXYPHENYL)SULFANYL] 2 METHYLPROPANAL; 3 [(4 CHLOROPHENYL)SULFANYL] 2 METHYLPROPANAL; 3 [(4 METHOXYPHENYL)SULFANYL] 2 METHYLPROPANAL; 3 METHYLPENTADECAN 2 OL; 3 METHYLTRIDECAN 2OL; DECANOL; LEWIS ACID; PHEROMONE; PROPIONALDEHYDE; REAGENT; TITANIUM DERIVATIVE; UNCLASSIFIED DRUG; ZINC DERIVATIVE;

ADDITION REACTION; ARTICLE; DIASTEREOISOMER; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 5644248089     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.09.005     Document Type: Article

References (35)

1. S. Byström, H.-E. Högberg, and T. Norin Tetrahedron 37 1981 2249 2254
2. (b) Mori, K. The Synthesis of Insect Pheromones 1979-1989. In The Total Synthesis of Natural Products; ApSimon, J., Ed. John Wiley & Sons: Ottawa, 1992; Vol. 9, pp 98-130.
3. R.M. Giblin-Davis, R. Gries, G. Gries, E. Pena-Rojas, I. Pinzon, J.E. Pena, A.L. Perez, H.D. Pierce, and A.C. Oehlschlager J. Chem. Ecol. 23 1997 2287 2298
4. A. Tai, Y. Higashiura, M. Kakizaki, T. Naito, K. Tanaka, M. Fujita, T. Sugimura, H. Hara, and N. Hayashi Biosci. Biotechnol. Biochem. 62 1998 607 608
5. S. Karlsson, and E. Hedenström Acta Chem. Scand. 53 1999 620 630
6. Y. Nakamura, and K. Mori Eur. J. Org. Chem. 1999 2175 2182
7. M. Larsson, B.-V. Nguyen, H.-E. Högberg, and E. Hedenström Eur. J. Org. Chem. 2001 353 363 and references cited therein
8. D. Tanner, and P. Somfai Tetrahedron 43 1987 4395 4406
9. A. Takle, and P. Kocienski Tetrahedron 46 1990 4503 4516
10. T. Harada, Y. Matsuda, S. Imanaka, and A. Oku J. Chem. Soc., Chem. Commun. 22 1990 1641 1643
11. K. Yamamoto, Y. Shiinoki, J. Furukawa, and S. Nakamura Chem. Pharm. Bull. 39 1991 1436 1439
12. T. Sunazuka, R. Obata, L. Zhuorong, S. Takamatsu, K. Komiyama, and S. Omura Tetrahedron Lett. 35 1994 2635 2636
13. R.F. Middleton, G. Foster, R.J.P. Cannell, P.J. Sidebottom, N.L. Taylor, D. Noble, M. Todd, J. Dawson, and G.C. Lawrence J. Antibiot. 48 1995 311 316
14. K. Makino, K.-I. Kimura, N. Nakajima, S.-I. Hashimoto, and O. Yonemitsu Tetrahedron Lett. 37 1996 9073 9076
15. D.A. Evans, and A.S. Kim Tetrahedron Lett. 38 1997 53 56
16. S.D. Marino, M. Iorizzi, E. Palagiano, F. Zollo, and C. Roussakis J. Nat. Prod. 61 1998 1319 1327
17. S.A. Kozmin Org. Lett. 3 2001 755 758
18. R. Baker, R.H.O. Boyes, D.M.P. Broom, J.A. Devlin, and C.J. Swain J. Chem. Soc. Chem. Commun. 1983 829 831
19. K. Mori, H. Kiyota, and D. Rochat Liebigs Ann. Chem. 8 1993 865 870
20. K. Mori, H. Kiyota, C. Malosse, and D. Rochat Liebigs Ann. Chem. 11 1993 1201 1204
21. B. Koutek, L. Streinz, and M. Romanuk Collect. Czech. Chem. Commun. 63 1998 899 954
22. S. Karlsson, and H.-E. Högberg Synthesis 2000 1863 1867
23. D.J. Cram, and F.A.A. Elhafez J. Am. Chem. Soc. 74 1952 5828 5835
24. D.J. Cram, and D.R. Wilson J. Am. Chem. Soc. 85 1963 1245 1249
25. M. Larsson, and H.-E. Högberg Tetrahedron 57 2001 7541 7548
26. M. Larsson, J. Andersson, R. Liu, and H.-E. Högberg Tetrahedron: Asymmetry 15 2004 2907 2915
27. V.S. Safont, V. Moliner, M. Olivia, R. Castillo, J. Andrés, F. González, and M. Carda J. Org. Chem. 61 1996 3467 3475
28. Anderbrant, O.; Östrand, F.; Lyytikäinen-Saarema, P.; Bergström, G.; Wassgren, A.-B.; Högberg, H.-E.; Hedenström, E.; Nguyen, B.-V.; Larsson, M.; Karlsson, S.; Varama, M.; Sierpinski, A.; Kolk, A.; Slusarski, S.; Bystrowski, K.; Herz, A.; Heitland, W.; Auger-Rosenberg, M.-A.; Geri, C.; Baronio, P.; Baldassari, N. Final report of the project PHERODIP supported by the European Community, FAIR1-CT95-0399 and IC20-CT96-0090: pine sawfly pheromones for sustainable management of European forests, 1999; pp 93-96.
29. E. Hedenström, H. Edlund, S. Lund, M. Abersten, and D. Persson J. Chem. Soc., Perkin Trans. 1 2002 1810 1817
30. E. Vedejs, R.A. Buchanan, P.C. Conrad, G.P. Meier, M.J. Mullins, J.G. Schaffhausen, and C.E. Schwartz J. Am. Chem. Soc. 111 1989 8421 8430
31. J.C. Carretero, and E. Dominguez J. Org. Chem. 57 1992 3867 3873
32. G. Magnusson Tetrahedron 34 1978 1385 1388
33. E. Hedenström, H.-E. Högberg, A.-B. Wassgren, G. Bergström, J. Löfqvist, B. Hansson, and O. Anderbrant Tetrahedron 48 1992 3139 3146
34. J. Matt, and E.P. Gunther J. Am. Chem. Soc. 77 1955 3655 3656
35. T. Sakai, S. Matsumoto, S. Hidaka, N. Imajo, S. Tsuboi, and M. Utaka Bull. Chem. Soc. Jpn 64 1991 3473 3475