Cp*Co(III)-Catalyzed γ-Selective C-H Allylation/Hydroamination Cascade for the Synthesis of Dihydroisoquinolines.

Cp*Co(III)-Catalyzed γ-Selective C-H Allylation/Hydroamination Cascade for the Synthesis of... A Cp*Co(III)-catalyzed γ-selective C-H allylation/hydroamination cascade toward the synthesis of 3,4-dihydroisoquinolines (DHIQs) has been successfully developed, starting from NH ketimines and allyl carbonates. Notably, highly efficient and γ-selective C-H allylations were accomplished using γ-substituted allyl reagents, thus overcoming the issues of poor α/γ selectivity and low reactivity of previous transition metal-catalyzed C-H allylations. The stereochemistry of allyl carbonates was a crucial factor, and synthesis of the DHIQs was achieved using (Z)-allyl carbonates. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Organic letters Pubmed

Cp*Co(III)-Catalyzed γ-Selective C-H Allylation/Hydroamination Cascade for the Synthesis of Dihydroisoquinolines.

Organic letters, Volume 21 (24): 5 – Dec 20, 2019
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Cp*Co(III)-Catalyzed γ-Selective C-H Allylation/Hydroamination Cascade for the Synthesis of Dihydroisoquinolines.

Organic letters, Volume 21 (24): 5 – Dec 20, 2019

Abstract

A Cp*Co(III)-catalyzed γ-selective C-H allylation/hydroamination cascade toward the synthesis of 3,4-dihydroisoquinolines (DHIQs) has been successfully developed, starting from NH ketimines and allyl carbonates. Notably, highly efficient and γ-selective C-H allylations were accomplished using γ-substituted allyl reagents, thus overcoming the issues of poor α/γ selectivity and low reactivity of previous transition metal-catalyzed C-H allylations. The stereochemistry of allyl carbonates was a crucial factor, and synthesis of the DHIQs was achieved using (Z)-allyl carbonates.
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DOI
10.1021/acs.orglett.9b03977

Abstract

A Cp*Co(III)-catalyzed γ-selective C-H allylation/hydroamination cascade toward the synthesis of 3,4-dihydroisoquinolines (DHIQs) has been successfully developed, starting from NH ketimines and allyl carbonates. Notably, highly efficient and γ-selective C-H allylations were accomplished using γ-substituted allyl reagents, thus overcoming the issues of poor α/γ selectivity and low reactivity of previous transition metal-catalyzed C-H allylations. The stereochemistry of allyl carbonates was a crucial factor, and synthesis of the DHIQs was achieved using (Z)-allyl carbonates.

Journal

Organic lettersPubmed

Published: Dec 20, 2019

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