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Asymmetric synthesis of chiral 1,2-oxazinane and hexahydropyridazin spirocyclic scaffolds by organocatalytic [4 + 2] cycloaddition† † Electronic supplementary information (ESI) available. CCDC 2153627, 2153695. For ESI and crystallographic data in CIF or other electronic format see https://doi.org/10.1039/d2ra02759c

ABSTRACT: A novel approach to synthesize chiral 1,2-oxazinane spirocyclic scaffolds by organocatalytic [4 + 2] cycloaddition reaction between methyleneindolinones and γ-aminooxy-α,β-unsaturated ester has been disclosed. Furthermore, a hydrazide 1,4-synthon is designed and synthesized to construct chiral hexahydropyridazin spirocyclic scaffolds with methyleneindolinones via [4 + 2] cycloaddition reaction. Both reactions give corresponding products in good to excellent yield, excellent diastereoselectivity and good enantioselectivity. Chiral 1,2-oxazinane spiro-oxindole and chiral hexahydropyridazin spiro-oxindole skeletons are made through asymmetric organocatalytic reactions. Corresponding products were produced in good to excellent yield, excellent diastereoselectivity and good enantioselectivity.

SUBMITTER: Tian H

PROVIDER: S-EPMC9128346 | biostudies-literature | 2022 May

REPOSITORIES: biostudies-literature

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