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A new protecting group for the carbonyl function

✍ Scribed by E.J. Corey; E.J. Trybulski; J. William Suggs

Publisher: Elsevier Science
Year: 1976
Tongue: French
Weight: 201 KB
Volume: 17
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)93936-4

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✦ Synopsis

During the course of various synthetic projects under study in these Laboratories we have had occasion to devise and apply a number of new methods for the protection of hydroxyl' , carbony and la&one' functions.

4 We now wish to report some recent results on the protection of aldehydes and ketones by conversion to 5,5-dlbromo-1,3-dioxane derivatives. This method introduces no new chirality, affords protection of the carbonyl group against many reagents with which it normally reacts (e.g., NaBHq, peracids, diborane), and allows efficient deprotection under neutral conditions by a highly selective reduction.

5 Zinc-silver couple has been found to be an unusually effective reagent for cleavage of the

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