Studies on 1,3-allylic strain control on dihydroxylations and hydrogenations of α-substituted enoates

Tetrahedron Letters

Volumn 38, Issue 17, 1997, Pages 3103-3106

  Kauppinen, Pasi M ^a   Koskinen, Ari M P ^a  

^a UNIVERSITY OF OULU   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANEDIOL DERIVATIVE; ISOXAZOLE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030990982     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00556-X     Document Type: Article

References (23)

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11. All new compounds gave satisfactory spectral and analytical (HRMS or elemental analysis) data.
12. a) Cha, J.K.; Christ, W.J.; Kishi, Y. Tetrahedron Lett. 1983, 24, 3943.
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14. 1H-NMR spectra were analyzed . Observed vicinal coupling constant of 9.9 Hz between H-5 and H-4 indicated the stereochemistry be as shown. equation presented
15. 2 and resulting heterogeneous mixture was stirred for 2h. Mixture was then filtered trough short pad of celite and solvents were evaporated to give hydrogenated product as clear oil (99%).
16. 1HNMR or HPLC. Proof of stereochemistry was obtained by converting 15 to known compound 18 and its spectra was examined (ref. 2). equation presented
17. Interestingly, hydrogenation of L-serine derived didehydroamino acid derivative with Pd/C in i-propanol proceeded with excellent selectivity (96:4). Avenoza, A.; Cativiela, C.; Peregrina, J.M.; Zurbano, M.M. Tetrahedron: Asymmetry 1996, 7, 1555.
18. a) Rylander, P. N. Catalytic Hydrogenation in Organic Synthesis; Academic Press: New York, 1979.
19. b) Rylander, P.N. Hydrogenation Methods, Academic Press: New York, 1985.
20. c) Siegel, S. in 'Comprehensive Organic Synthesis', ed. Trost, B.M. Pergamon, 1991, vol 8, chapter 3.1.
21. a) The order of decreasing activity to promote isomerization is Pd≫ Rh, Ru, Pt > Ir, Nishimura, S.; Sakamoto, H.; Ozawa, T. Chem. Lett. 1973, 855.
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23. c) In our hands no hydrogenation occurred with Ir/C on experiments with either 8 or 9.