Deuterium-isotope study on the reductive ring opening of benzylidene acetals.
نویسندگان
چکیده
Specific deuterated reference compounds were prepared to probe the stereoselectivity of the reductive ring opening of carbohydrate-based benzylidene-type acetals. AlD(3) revealed a retentive stereoselectivity probably through the rare S(N)i (internal nucleophilic substitution) mechanism. An S(N)1-like mechanism occurs in the acid-promoted regioselective BD(3)·THF- or Et(3)SiD-reductive ring opening.
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ورودعنوان ژورنال:
- Organic & biomolecular chemistry
دوره 9 22 شماره
صفحات -
تاریخ انتشار 2011