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Concerning directed oxidation and transacylation during a general approach to hydroxylated lactams

✍ Scribed by Jeremy Robertson; Emilia Abdulmalek

Book ID: 104096438
Publisher: Elsevier Science
Year: 2009
Tongue: French
Weight: 469 KB
Volume: 50
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2009.03.084

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✦ Synopsis

A variant of Knight's route to D-mannolactam, exploring the stereoselectivity of directed oxidation conditions, reveals a tendency for hydroxylated N-tosyl lactams to rearrange to c-lactones. An attempted directed dihydroxylation in this series is shown to result in unexpectedly high anti-selectivity.

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Treatment of primary, secondary or tertiary 7-and b-hydroxyolefins with cetyltrimethylammonium permanganate gives good yields of 7-and 6-lactones by oxidative cyclization, with loss of one carbon.