Synthesis and ring-opening reactions of the diastereoisomeric cis- and trans-epoxides derived from 3-(Benzyloxy)cyclopentene and 2-(Benzyloxy)-2,5- dihydrofuran

European Journal of Organic Chemistry

Volumn , Issue 8, 1998, Pages 1675-1686

  Crotti, Paolo ^a   Di Bussolo, Valeria ^a   Favero, Lucílla ^a   Macchia, Franco ^a   Pineschi, Mauro ^a  

^a UNIVERSITY OF PISA   (Italy)

Author keywords

Epoxides ; Nucleophilic additions ; Regioselectivity ; Synthetic methods

Indexed keywords

EID: 0000659064     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(199808)1998:8<1675::AID-EJOC1675>3.0.CO;2-B     Document Type: Article

References (38)

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27. The result obtained with PBIA is in agreement with a preferential attack of the electrophile on the face of olefin 18 opposite to the OBzl substituent, as observed in the case of 8.
28. 2O) with both the exocyclic and the endocyclic oxygens of the acetal functionality, as tentatively shown (see below).
29. + cation of the reagent. The same reaction carried out in the presence of a crown ether (12-crown-4) should however be considered as operating under non-chelating conditions, due to the sequestering ability of the crown ether specific for Li+.
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35. 17
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37. 1H-NMR spectra, with appropriate double resonance experiments, the C-I product regiochemistry can be unequivocally assigned to bromohydrin 12 and compounds 39-47, while the C-2 product regiochemistry can be assigned to bromohydrin 9, as shown in Scheme 4.
38. 4 solution can be expected to be quite similar (presence of only a free OH) to those of the obtained regioisomeric C-1 products (see text and Table 3).