Paper
A novel synthesis of enantiopure octahydropyrrolo[3,4-b]pyrroles by intramolecular [3 + 2] dipolar cycloaddition on chiral perhydro-1,3-benzoxazines.
Published 2002 · Rafael Pedrosa, Celia Andrés, Laura de las Heras
Organic letters
18
Citations
0
Influential Citations
Abstract
[reaction: see text] Condensation of N-substituted glycines with chiral 3-allyl-2-formyl perhydro-1,3-benzoxazines forms an azomethine ylide that cyclizes to give octahydropyrrolo[3,4-b]pyrrole derivatives. The [3 + 2] dipolar cycloadditions are stereoespecific leading to a single diastereoisomer. The chemical yields are dependent on the reaction temperature and the presence or absence of a base.
This novel synthesis of enantiopure octahydropyrrolo[3,4-b]pyrroles enables the synthesis of chiral perhydro-1,3-benzoxazines, with a single diastereoisomer and varying yields
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