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Iridium-catalyzed asymmetric ring-opening reactions of oxabicyclic alkenes with secondary amine nucleophiles.

ABSTRACT: Iridium-catalyzed asymmetric ring-opening reactions of oxabicyclic alkenes with various aliphatic and aromatic secondary amines are reported for the first time. The reaction gave the corresponding trans-1,2-dihydronaphthalenol derivatives in good yields with moderate enantioselectivities in the presence of 2.5 mol % [Ir(COD)Cl](2) and 5 mol % bisphosphine ligand (S)-p-Tol-BINAP. The trans-configuration of 3f was confirmed by X-ray crystallography.

SUBMITTER: Yang D

PROVIDER: S-EPMC2814328 | biostudies-literature | 2009 Oct

REPOSITORIES: biostudies-literature

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Iridium-catalyzed asymmetric ring-opening reactions of oxabicyclic alkenes with secondary amine nucleophiles.

Yang Dingqiao D Hu Ping P Long Yuhua Y Wu Yujuan Y Zeng Heping H Wang Hui H Zuo Xiongjun X

Beilstein journal of organic chemistry 20091009

Iridium-catalyzed asymmetric ring-opening reactions of oxabicyclic alkenes with various aliphatic and aromatic secondary amines are reported for the first time. The reaction gave the corresponding trans-1,2-dihydronaphthalenol derivatives in good yields with moderate enantioselectivities in the presence of 2.5 mol % [Ir(COD)Cl](2) and 5 mol % bisphosphine ligand (S)-p-Tol-BINAP. The trans-configuration of 3f was confirmed by X-ray crystallography. ...[more]

PMID: 20126558

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