The catalytic Shapiro reaction

Journal of the American Chemical Society

Volumn 118, Issue 9, 1996, Pages 2289-2290

  Maruoka, Keiji ^a,b   Oishi, Masataka ^a   Yamamoto, Hisashi ^a  

^a NAGOYA UNIVERSITY   (Japan)

^b HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029932282     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja951422p     Document Type: Article

References (13)

1. Reviews: (a) Shapiro. R. H. Org. React. 1976, 23, 405. (b) Adlington, R. M.: Barrett, A. G. M. Acc. Chem. Res. 1983. 16. 55. (c) Chamberlin, A. R.; Bloom, S. H. Org. React. 1990, 39, 1.
2. Reviews: (a) Shapiro. R. H. Org. React. 1976, 23, 405. (b) Adlington, R. M.: Barrett, A. G. M. Acc. Chem. Res. 1983. 16. 55. (c) Chamberlin, A. R.; Bloom, S. H. Org. React. 1990, 39, 1.
3. Reviews: (a) Shapiro. R. H. Org. React. 1976, 23, 405. (b) Adlington, R. M.: Barrett, A. G. M. Acc. Chem. Res. 1983. 16. 55. (c) Chamberlin, A. R.; Bloom, S. H. Org. React. 1990, 39, 1.
4. Bamford-Stevens reaction of ketone phenylaziridinylhydrazones: (a) Mohamadi, F.: Collum, D. B. Tetrahedron Lett. 1984, 25, 271. (b) Sarkar, T. K.: Ghorai, B. K. J. Chem. Soc., Chem. Commun. 1992, 1184.
5. Bamford-Stevens reaction of ketone phenylaziridinylhydrazones: (a) Mohamadi, F.: Collum, D. B. Tetrahedron Lett. 1984, 25, 271. (b) Sarkar, T. K.: Ghorai, B. K. J. Chem. Soc., Chem. Commun. 1992, 1184.
6. Shapiro reaction of ketone phenylaziridinylhydrazones with excess base: Evans, D. A.: Nelson. J. V. J. Am. Chem Soc. 1980, 102, 774.
7. Muller, R. K.; Joos, R.: Felix, D.; Schreiber, J.: Wintner, C.: Eschenmoser, A. Organic Syntheses; Wiley: New York. 1988; Collect. Vol. VI, p 56.
8. 13C NMR analysis: Bunnell, C. A.: Fuchs, P. L. J. Org. Chem. 1977, 42, 2614.
9. Prepared from optically pure (R)-1-phenyl-1,2-ethanediol and purified by recrystallizarion of 1-amino-2-phenylaziridinium acetate according to the procedure in ref 4.
10. 3)}: Honda, T.; Kimura, N.: Tsubuki, M. Tetrahedron: Asymmetry 1993, 4, 21.
11. Minks, A. K.; Voerman, S. Entomol. Exp. Appl. 1973, 16, 541.
12. Decomposition of (Z)-hydrazone 11 with catalytic LDA proceeds regioselectively due to syn-directing effect: Augeri, D. J.: Chamberlin, A. R. Tetrahedron Lett. 1994, 35, 5599.
13. The isomeric purity of 12 was determined by capillry GLC analysis after conversion to the epoxide with MCPBA. The authentic sample of 12 was prepared from 9-tetradecyn-1-ol by hydrogenation over P2-Ni with subsequent acetylation of (Z)-enol (cis-selectivity = 98.8%): Hoskovec. M.: Saman, D.: Koutek, B. Collect. Czech. Chem. Commun. 1990, 55, 2270.