✦ LIBER ✦
Lewis acid catalyzed rearrangements of structurally related α,β-unsaturated epoxy ketones and oximes. A complementary approach to the synthesis of isomeric 1,4-diketospiro[n,m] alkanes.
✍ Scribed by Robert D. Bach; Mark W. Tubergen; Russell C. Klix
- Publisher
- Elsevier Science
- Year
- 1986
- Tongue
- French
- Weight
- 246 KB
- Volume
- 27
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
Lew~'s acid catal.vzed rearrangement of cr,B-epoxy o.yimes proceeds b_v oxl'rane cleavage u to the oxime moiety with an attendant pinacol t_vpe alkyd roigration to the resonance stabilized carbenium ion at C, affording a I,_%d2'keto-monoxl'me.
Recent mechanistic studies have provided cogent arguments that carbonyl migrations in u,B-epoxy ketones derived from acyclic enones and their related chlorohydrins are concerted rearrangements that proceed with inversion of configuration at the migration terminus. lp2 Our