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Chiral dienolate chemistry in remote asymmetric induction: the allylation / cope rearrangement sequence leading to γ-chiral α, β-unsaturated acid derivatives

✍ Scribed by Katsuhiko Tomooka; Atsushi Nagasawa; Shih-Yi Wei; Takeshi Nakai

Publisher
Elsevier Science
Year
1996
Tongue
French
Weight
279 KB
Volume
37
Category
Article
ISSN
0040-4039

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✦ Synopsis

The allylation of the dienolate derivedfrom the chiral a, p-orfl, ~unsaturated imidefollowed by the Cope rearmngement is shown to effect the net remote symmetric induction to create anew chirality of eitherconfiguration at the yposition in high 70 de. The utility of this qproach is shown in the mymmetrk synthesis of the C6 side chain of zaragozic acid A.

📜 SIMILAR VOLUMES

Chiral dienolate-based remote asymmetric
Chiral dienolate-based remote asymmetric induction: The asymmetric α-oxylation/Pd(0)-catalyzed allylic substitution sequence leading to γ-chiral α, β-unsaturated acid derivatives
✍ Masaharu Sugiura; Yasuhiro Yagi; Shih-Yi Wei; Takeshi Nakai 📂 Article 📅 1998 🏛 Elsevier Science 🌐 French ⚖ 238 KB

The asymmetric a-oxylation of the dienolates derived from chiral or, d-or fl, T-unsaturated imide with dibenzyl peroxydicarbonate followed by the Pd(O)catalyzed reactions of the resulting allylic carbonate with various nucleophiles (alkylation, etherification, and amination) is shown to provide the

ChemInform Abstract: Chiral Dienolate-Ba
ChemInform Abstract: Chiral Dienolate-Based Remote Asymmetric Induction: The Asymmetric α-Oxylation/Pd(0)-Catalyzed Allylic Substitution Sequence Leading to γ-Chiral α,β-Unsaturated Acid Derivatives.
✍ M. SUGIURA; Y. YAGI; S.-Y. WEI; T. NAKAI 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 44 KB 👁 1 views

The dienolates derived from the chiral imides (I) and (IV) undergo asymmetric α-oxylation with dibenzyl peroxydicarbonate to give the (E)-or (Z)-products (III) and (V) highly selectively. Both undergo thermal rearrangements to provide the γ-(S)-or γ-(R)-oxy-substituted derivatives with efficient asy