Fluoride-catalyzed aldol reaction of ethyl trimethylsilyldiazoacetate with aldehydes leading to ethyl α-diazo-β-hydroxy esters and rhodium catalyzed decarboxylative rearrangement of diazo urethanes leading to β- amino acrylates

Tetrahedron Letters

Volumn 40, Issue 27, 1999, Pages 5059-5062

  Kanemasa, Shuji ^a   Araki, Takahiro ^a   Kanai, Toshio ^a   Wada, Eiji ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLIC ACID DERIVATIVE; ALDEHYDE DERIVATIVE; ESTER DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL INTERACTION; CHEMICAL MODIFICATION; CHEMICAL REACTION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033516610     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00933-8     Document Type: Article

References (20)

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5. Nomura, K.; Iida, T.; Hori, K.; Yoshii, E. J. Org. Chm. 1994, 59,488-490.
6. Kanemasa, S.; Kanai, T.; Araki, T.; Wada, E. Tetrahedron Lett. 1999, 40, 5055-5058.
7. (a) Wenkert, E.; McPherson, C. A. J. Am. Chem. Soc. 1972, 94, 8084-8090.
8. (b) Schöllkopf, U.; Banhidai, B.; Frasnelli, H.; Meyer, R.; Backhaus, H. Liebigs Ann. Chem. 1974, 11, 1767-1783.
9. (c) Pellicciari, R.; Natalini, B. J. Chem. Soc. Perkin Trans. 1 1977, 1822-1824.
10. (d) Pellicciari, R.; Natalini, B.; Cecchetti, S.; Fringuelli, R. J. Chem. Soc. Perkin Trans. 1 1985, 493-498.
11. Recent work using metalated diazo esters: Padwa, A.; Sa, M. M.; Weingarten, M. D. Tetrahedron 1997, 53, 2371-2386.
12. Cyanide ion catalyzed aldol reactions of diazo esters are known: Evans, D. A.; Truesdale, L. K.; Grimm, K. G. J. Org. Chem. 1976, 41, 3335-3336.
13. 4 and evaporated under vaccum. The resulting residue was chromatographed on silica gel with hexane - ethyl acetate (5:1 v/v) to give the adduct 3a (0.183 g, 83%) as yellow oil.
14. 4 to activate the acceptor molecule was totally ineffective.
15. Calter, M. A.; Sugathapala, P. M.; Zhu, C. Tetrahedron Lett. 1997, 38, 3837-3840
16. 2, 0 °C - rt, 16 h.
17. 2, rt, 16 h) all failed leading to decomposition of 4.
18. 2) and the filtrate was washed with saturated aqueous NaCl. The dichloromethane was dried over magnesium sulfate and evaporated in vacuo to give colorless solid of 4a (Y = 96%).
19. Rhodium catalyzed reaction of α-diazo-β-hydroxy esters leading to β-keto esters is known: Pellicciari, R.; Fringuelli, R.; Sisani, Ettore; C., M. J. Chem. Soc. Perkin Trans. 1 1981, 2566-2569.
20. 4S: C, 62.59; H, 5.54; N, 4.06%.