Benzothiazoles as carbonyl equivalents

✍ Scribed by E.J. Corey; Dale L. Boger

• Book ID: 104240291
• Publisher: Elsevier Science
• Year: 1978
• Tongue: French
• Weight: 284 KB
• Volume: 19
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)88967-x

✦ Synopsis

The objective of the investigation described in this and the following papers was to develop methodology for the conversion of cyclic ketones to Spiro and fused annulation products not readily accessible by conventional methods1 (e.g., cyclohexanone -f A'-3-octalone).

Our approach centered on two key synthetic operations: (1) the conversion of cyclic ketones to synthetic equivalents of formyl stabilized anions, illustrated by 1 and 2, and (2) the conversion of cyclic ketones to synthetic equivalents of formyl substituted Michael acceptors (2). Special properties are required for the formyl equivalent in each case; for example, it should be noted that u,B-unsaturated aldehydes tend to react with carbon nucleophiles (even cuprates) as carbonyl rather than Michael acceptors.'