Abstract
The allylation of the dienolate derived from the chiral α, β- or β,γ-unsaturated imide followed by the Cope rearrangement is shown to effect the net remote asymmetric induction to create a new chirality of either configuration at the γ-position in high % de. The utility of this approach is shown in the asymmetric synthesis of the C6 side chain of zaragozic acid A. Copyright (C) 1996 Elsevier Science Ltd.
| Original language | English |
|---|---|
| Pages (from-to) | 8895-8898 |
| Number of pages | 4 |
| Journal | Tetrahedron Letters |
| Volume | 37 |
| Issue number | 49 |
| DOIs | |
| Publication status | Published - Dec 2 1996 |
| Externally published | Yes |
All Science Journal Classification (ASJC) codes
- Biochemistry
- Drug Discovery
- Organic Chemistry
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Cite this
Tomooka, K., Nagasawa, A., Wei, S. Y., & Nakai, T. (1996). Chiral dienolate chemistry in remote asymmetric induction: The allylation/Cope rearrangement sequence leading to γ-chiral α,β-unsaturated acid derivatives. Tetrahedron Letters, 37(49), 8895-8898. https://doi.org/10.1016/S0040-4039(96)02077-1