Tetrahedron Letters p. 2531 - 2534 (1998)
Update date:2022-08-11
Topics:
Dimitroff, Martin
Fallis, Alex G.
The facial influence and synthetic utility of oxygen, sulfur and carbon atoms adjacent to the ketone in the series of α-spiro ketones 2, 3, and 4 upon nucleophilic addition has been examined. Addition to the carbonyl group displayed a preference for attack anti to the heteroatom in competition with carbon in synthetically useful ratios. Hydride reduction of 2 with chelating reagenst (NaBH4, LiAlH4 etc.) reversed this facial preference.
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