Electronic effect on the regioselectivity in the ring opening of para-substituted phenyloxiranes by acetylides

Tetrahedron Letters

Volumn 45, Issue 50, 2004, Pages 9265-9268

  Shindo, Mitsuru ^a   Sugioka, Tomoyuki ^a   Shishido, Kozo ^a  

^a UNIVERSITY OF TOKUSHIMA   (Japan)

Author keywords

Alkynylation; Electronic effect; Lewis acid; Oxirane; Regioselectivity

Indexed keywords

ACETIC ACID DERIVATIVE; ALKANE DERIVATIVE; HALIDE; LITHIUM CHLORIDE; PHENYL GROUP; TITANIUM;

ALKYLATION; ARTICLE; ELECTRONICS; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; MOLECULAR MECHANICS; REACTION ANALYSIS; RING OPENING; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SUBSTITUTION REACTION;

EID: 8544222635     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.10.049     Document Type: Article

References (23)

1. For reviews, see: R.E. Parker, and N.S. Isaacs Chem. Rev. 59 1959 737 799
2. J.G. Smith Synthesis 1984 629 656
3. M. Yamaguchi B.M. Trost I. Fleming Comprehensive Organic Synthesis Vol. 1.11 1991 Pergamon Oxford 342 345
4. Recent examples, see: W.-M. Dai Tetrahedron 54 1998 12497 12512
5. A. Ramacciotti, R. Fiaschi, and E. Napolitano Tetrahedron: Asymmetry 7 1996 1101 1104
6. A. Herunsalee, M. Isobe, Y. Fukuda, and T. Goto Synlett 1990 701 702
7. M. Yamaguchi, and I. Hirao Tetrahedron Lett. 24 1983 391 394
8. N. Krause, and D. Seebach Chem. Ber. 120 1987 1845 1851
9. N. Krause, and D. Seebach Chem. Ber. 121 1988 1315 1320
10. Y. Fukuda, S. Matsubara, C. Lambert, H. Shiragami, T. Nanko, K. Utimoto, and H. Nozaki Bull. Chem. Soc. Jpn. 64 1991 1810 1813
11. M. Chini, P. Crotti, L. Favero, and F. Macchia Tetrahedron Lett. 32 1991 6617 6620
12. The substituent effect on the reactions of non-carbon nucleophiles and malonates has been reported, see: R. Fuchs, and C.A. VanderWerf J. Am. Chem. Soc. 76 1954 1631 1634
13. M.M. Kayser, and P. Morand Can. J. Chem. 58 1980 302 306 See also Ref. 1a
14. 2)
15. C. Hansch, A. Leo, and R.W. Taft Chem. Rev. 91 1991 165 195
16. O. Pàmies, and J-E. Bäckvall J. Org. Chem. 67 2002 9006 9010 The enantiomeric excess was determined by HPLC analysis on a Daicel CHIRAL PAK AD-H column
17. The enantiomeric excess was determined by HPLC analysis on a Daicel CHIRAL PAK AD-H column. The absolute configuration was confirmed by comparison of the sign of the specific rotation with the literature value of 17 derived from 3. (R)-17: Y. Nagao, T. Kumagai, S. Yamada, E. Fujita, Y. Inoue, Y. Nagase, S. Aoyagi, and T. Abe J. Chem. Soc., Perkin Trans. 1 1985 2361 2367
18. ® Si, ethyl acetate/hexane) to afford 188 mg (85%) of 4 (X = H)
19. J. Meinwald, S.S. Labana, and M.S. Chadha J. Am. Chem. Soc. 85 1963 582 585
20. 4 and concentrated in vacuo to give a crude mixture, which was purified with preparative HPLC (LiChrosorb® Si, ethyl acetate/hexane) to afford 206 mg (82%) of 3 (X = OMe)
21. M. Yamaguchi, Y. Nobayashi, and I. Hirao Tetrahedron 40 1984 4261 4266
22. Without Lewis acids, the alkynylation does not proceed. See Ref. 5
23. N1 like reaction involving a carbocation intermediate