Enantio- and Diastereoselective Synthesis of Homoallylic α-Trifluoromethyl Amines by Catalytic Hydroalkylation of Dienes.

Journal Article (Journal Article)

We describe a strategy for the enantio- and diastereoselective synthesis of homoallylic α-trifluoromethyl amines by the catalytic hydroalkylation of terminal dienes. Trifluoromethyl-substituted isatin-derived azadienolate nucleophiles undergo γ-selective alkylation with a Pd-DTBM-SEGPHOS catalyst, which additionally promotes regioselective addition to the diene and delivers products in up to 86% yield, 10:1 dr, and 97.5:2.5 er.

Full Text

Duke Authors

Malcolmson, Steven

Cited Authors

Onyeagusi, CI; Shao, X; Malcolmson, SJ

Published Date

February 2020

Published In

Organic Letters

Volume / Issue

22 / 4

Start / End Page

1681 - 1685

PubMed ID

32013445

Pubmed Central ID

PMC7079280

Electronic International Standard Serial Number (EISSN)

1523-7052

International Standard Serial Number (ISSN)

1523-7060

Digital Object Identifier (DOI)

10.1021/acs.orglett.0c00342

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