Intermolecular Diels-Alder additions of the readily available dienamides 3 to various dienophiles proceeded in a regio-and stereoselective manner, allowing the preparatTon of complex anilides (z), cyclohexenyl amides (2, 8) and bridged heterocycles (13).
β¦ LIBER β¦
N-acyl-1-amino-1,3-dienes: 1-amino-1,3-diene synthetic equivalents for the diels-alder reaction
β Scribed by Larry E. Overman; Garry F. Taylor; Peter J. Jessup
- Publisher
- Elsevier Science
- Year
- 1976
- Tongue
- French
- Weight
- 248 KB
- Volume
- 17
- Category
- Article
- ISSN
- 0040-4039
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R2AlC~-ordinate ~-meth~~loy~ul~ lc undergoes efficient, t&o-selective and highly diastereofact controlled [4+2]-additions to cyclopentadiene, isoprene, fE)-piperylene and the 2-silyloxydieaes 10 and 12. The resulting crystalline cyclogdducts are smoothly reduced with LiAlH4 providing the recovered a