1.
J Org Chem
; 62(2): 275-286, 1997 Jan 24.
Artigo
em Inglês
| MEDLINE
| ID: mdl-11671399
RESUMO
The diastereoselectivity of 5-exo-trigonal cyclizations of 2-(4-penten-1-yl)-1,3-dioxolan-2-yl and 2-(4-penten-1-yl)-1,3-dioxan-2-yl radicals is investigated. When dioxolanes or dioxanes derived from C(2) symmetrically substituted diols are employed the diastereoselectivity is poor. In the dioxanyl series this is a consequence of the cyclization occurring through a twist-boat conformer. Disymmetrically substituted dioxanyl radicals, derived from the alcohols 21 and 41, are, however, constrained to chairlike conformations and accordingly give rise to highly diastereoselective cyclizations. Conditions are described for the hydrolysis of the resulting spiroacetals and for determination of the ee of the resulting 2-methylcyclopentanones.
2.
3.
Proc R Soc Med
; 65(9): 809-10, 1972 Sep.
Artigo
em Inglês
| MEDLINE
| ID: mdl-5085074