1,4-Asymmetric induction in the Nozaki-Hiyama reaction

Tetrahedron Letters

Volumn 37, Issue 31, 1996, Pages 5487-5490

  Maguire, Robert J ^a   Mulzer, Johann ^a   Bats, Jan W ^a  

^a GOETHE UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANOL;

ARTICLE; CRYSTALLOGRAPHY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030605862     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01161-6     Document Type: Article

References (16)

1. 1. a) Okude, Y.; Hirano, S.; Hiyama, T.; Nozaki, H.; J.Am.Chem.Soc., 1977, 99, 3179;
2. b) Buse, C.T.; Heathcock, C.H.; Tetrahedron Lett., 1978, 19, 1685; Hiyama, T.; Okude, Y.; Kimura, K.; Nozaki, H.; Bull.Chem.Soc.Jpn., 1982, 55, 561.
3. b) Buse, C.T.; Heathcock, C.H.; Tetrahedron Lett., 1978, 19, 1685; Hiyama, T.; Okude, Y.; Kimura, K.; Nozaki, H.; Bull.Chem.Soc.Jpn., 1982, 55, 561.
4. 2. e.g.a) Mulzer, J.; Kattner, L., Strecker A.R.; Schröder, C.; Buschmann, J.; Lehmann, C.; Luger, P; J.Am.Chem.Soc., 1991, 113, 4218;
5. b) Mulzer, J.; Kattner, L.; Angew.Chem.Int.Ed.Engl.; 1990, 29, 679.
6. 3 . e.g. a) Shibuya, H.; Ohashi, K.; Kawashima, K.; Hori, K.; Murakami, N.; Kitigawa, I.; Chem.Lett., 1986, 85;
7. b) Rayner, C.M.; Astles, P.C.; Paquette, L.A.; J.Am.Chem.Soc., 1992, 114, 3926.
8. 4. a) Nishigaichi, Y.; Takuwa, A.; Jodai, A.; Tetrahedron Lett., 1991, 32, 2383;
9. b) Nishigaichi, Y.; Kuramoto, H.; Takuwa, A.; Tetrahedron Lett., 1995, 36, 3353;
10. c) Gruttadauria, M.; Thomas, E.J.; J.Chem.Soc., Chem.Commun., 1995, 1469.
11. 5. Hatakeyama, S.; Numata, H.; Osani, K.; Takano, S.; J.Org.Chem., 1989, 54, 3515.
12. 6. Hoffmann, H.M.R.; Rabe, J.; Angew.Chem.Int.Ed.Engl., 1983, 22, 795.
13. 7 . Wessel, H.-P.; Iversen, T.; Bundle, D.R.; J.Chem.Soc., Perkin Trans 1, 1985, 2247.
14. 8. Nicolaou, K.C.; Veale, C.A.; Webber, S.E.; Katerinopoulos, H.; J.Am.Chem.Soc., 1985, 107, 7515..
15. 9. X-ray crystallographic data have been deposited with the Cambridge Cristallographic Data Centre. The data can be obtained, on request, from: The Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1 EZ, UK.
16. 3; 250 MHz): δ = 0.79 (3H, d, J6.8), 1.01 (3H, d, J6.5), 1.90 (1H, m), 2.44 (1H, dd, J15.4, 8.4), 2.57 (1H, dd, J15.4, 4.3), 3.31 (1H, d, J8.8), 4.20 and 4.48 (each 1H, d, J11.8), 4.97 (1H, dd, J8.4, 4.3), 5.08 (1H, d, J1.4), 5.14 (1H, d, J1.4) , 7.31 (10H, m).