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Construction of Azaspirocyclic Ketones through α-Hydroxyiminium Ion or α-Siloxy Epoxide Semipinacol Rearrangements

2001; American Chemical Society; Volume: 3; Issue: 13 Linguagem: Inglês

10.1021/ol0160708

1523-7060

Michaël D. B. Fenster, Brian O. Patrick, Gregory R. Dake,

Asymmetric Synthesis and Catalysis

[reaction: see text] Semipinacol-type rearrangements to produce azaspirocyclic ketones are presented. The yields and stereoselectivities of these reactions range from 67-94% yield and 2.8:1 to 1:0 diastereoselectivity, respectively.