Regiochemical control in intramolecular cyclization of methylene-interrupted epoxydiols
Regiochemical control in intramolecular cyclization of methylene-interrupted epoxydiols
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DOI：
10.1021/ol016118h
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发表时间：
2001-08-09
期刊：
影响因子：
5.2
通讯作者：
Borhan, B
中科院分区：
文献类型：
--
作者：
Narayan, RS;Sivakumar, M;Borhan, B
[GRAPHICS]Methylene-interrupted epoxydiols have multiple regiochemical routes for cyclization. The 5-exo process is the most prevalent under acidic conditions. However, the regioselectivity can be controlled by the appropriate choice of acid promoter and pendant groups adjacent to the epoxide. The 5-exo product is obtained exclusively without the presence of a carbocation-stabilizing pendant group. Alkenyl and thiophenyl groups adjacent to the epoxide alter the regioselectivity and enable access to the 5-endo tetrahydrofuran and 6-endo tetrahydropyran products.
