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Rapid Asymmetric Synthesis of Disubstituted Allenes by Coupling of Flow-Generated Diazo Compounds and Propargylated Amines.

ABSTRACT: We report herein the asymmetric coupling of flow-generated unstabilized diazo compounds and propargylated amine derivatives, using a new pyridinebis(imidazoline) ligand, a copper catalyst and base. The reaction proceeds rapidly, generating chiral allenes in 10-20?minutes with high enantioselectivity (89-98?% de/ee), moderate yields and a wide functional group tolerance.

SUBMITTER: Poh JS

PROVIDER: S-EPMC5363227 | biostudies-literature | 2017 Feb

REPOSITORIES: biostudies-literature

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Rapid Asymmetric Synthesis of Disubstituted Allenes by Coupling of Flow-Generated Diazo Compounds and Propargylated Amines.

Poh Jian-Siang JS Makai Szabolcs S von Keutz Timo T Tran Duc N DN Battilocchio Claudio C Pasau Patrick P Ley Steven V SV

Angewandte Chemie (International ed. in English) 20170111 7

We report herein the asymmetric coupling of flow-generated unstabilized diazo compounds and propargylated amine derivatives, using a new pyridinebis(imidazoline) ligand, a copper catalyst and base. The reaction proceeds rapidly, generating chiral allenes in 10-20 minutes with high enantioselectivity (89-98 % de/ee), moderate yields and a wide functional group tolerance. ...[more]

PMID: 28075518

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