An intramolecular hetero Diels-Alder reaction of α- (alkynylsiloxy)aldimine derivatives

Tetrahedron Letters

Volumn 41, Issue 30, 2000, Pages 5715-5718

  Shimizu, Tadashi ^a   Tanino, Keiji ^a   Kuwajima, Isao ^b  

^a HOKKAIDO UNIVERSITY   (Japan)

^b KITASATO UNIVERSITY   (Japan)

Author keywords

Alkynes; Carbamates; Diels Alder reactions; Imines; Oxazines; Quinolines

Indexed keywords

ALDEHYDE; ALKANEDIOL DERIVATIVE; CARBAMIC ACID DERIVATIVE; IMINE; QUINOLINE DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID;

ARTICLE; CHEMICAL REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

BETULACEAE;

EID: 0034702523     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00936-9     Document Type: Article

References (14)

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2. (b) Weinreb, S. M. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I. Eds. Pergamon: Oxford, 1991; Vol. 5, pp. 401-449.
3. (c) Boger, D. L. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I. Eds. Pergamon: Oxford, 1991; Vol. 5, pp. 451-512.
4. (d) Weinreb, S. M.; Scola, P. M. Chem. Rev. 1989, 89, 1525-1534.
5. Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I. Eds. Pergamon: Oxford, 1991; Vol. 5, pp. 513-550.
6. Tanino, K.; Shimizu, T.; Kuwahara, M.; Kuwajima, I. J. Org. Chem. 1998, 63, 2422-2423.
7. (a) Merten, R.; Muller, G. Angew. Chem. 1962, 74, 866-867.
8. (b) Tohyama, Y.; Tanino, K.; Kuwajima, I. J. Org. Chem. 1994, 59, 518-519.
9. 3) δ 13.93, 14.05, 19.64, 20.61, 20.69, 22.49, 22.61, 22.71, 27.56 (6C), 28.29, 28.44, 31.19, 31.54, 60.58, 60.83, 61.13, 76.36, 79.34, 111.19, 155.02, 155.42.
10. 3) δ 0.87 (t, J=7.1 Hz, 3 H), 0.91 (t, J=7.3 Hz, 3 H), 0.97 (s, 9 H), 1.18 (s, 9 H), 1.20-1.78 (m, 14 H), 2.45 (dt, J=1.6, 7.0 Hz, 2 H), 3.72-4.24 (m, 5 H), 4.92 (bs, 1 H).
11. (a) Linkart, F.; Laschat, S. Synlett 1994, 125-126.
12. (b) Linkart, F.; Laschat, S.; Knickmeier, M. Liebigs Ann. Chem. 1995, 985-983.
13. (c) Linkart, F.; Laschat, S.; Kotila, S.; Fox, T. Tetrahedron 1996, 52, 955-970.
14. 3) δ 14.12, 14.32, 20.56, 22.49, 22.65, 22.86, 27.87 (3C), 28.32 (3C), 28.66, 30.16, 30.74, 31.63, 37.77, 38.22, 55.48, 82.05, 102.79, 121.51, 125.58, 126.72, 131.05, 145.08, 152.68, 156.74, 169.47.