Tetrahedron Letters p. 2527 - 2530 (1998)
Update date:2022-08-11
Topics:
Dimitroff, Martin
Fallis, Alex G.
The facial influence and synthetic utility of oxygen and sulfur heteroatoms adjacent to carbocyclic ketones upon nucleophilic addition has been investigated. Addition to the carbonyl group displayed a preference for attack anti to sulfur and syn to oxygen in synthetically useful ratios. Diisopropylaluminum hydride reduction in the cyclopentanone series reversed this facial preference.
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