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A Simple Procedure for the Synthesis of ?-Hydroxyallenamides via Homoallenylation of Aldehydes.

ABSTRACT: A simple one-pot synthesis of ?-hydroxyallenamides is reported. This procedure entails chemo- and regioselective hydroboration of 3-en-1-ynyl-sulfonylamides with Cy2BH followed by homoallenylation of aldehydes to yield ?-hydroxyallenamides (up to 94% yield and >20:1 dr). Controlled synthesis of up to three continuous stereochemical elements was realized. Density functional theory (DFT) calculations suggest a concerted Zimmerman-Traxler chair-like transition state. Initial results suggest that enantio- and diastereoselective synthesis of ?-hydroxyallenamides with optically active hydroboration reagents is viable.

SUBMITTER: Kim BS

PROVIDER: S-EPMC5977997 | biostudies-literature | 2018 Apr

REPOSITORIES: biostudies-literature

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A Simple Procedure for the Synthesis of <i>β</i>-Hydroxyallenamides via Homoallenylation of Aldehydes.

Kim Byeong-Seon BS Gutierrez Osvaldo O Kozlowski Marisa C MC Walsh Patrick J PJ

Advanced synthesis & catalysis 20180130 7

A simple one-pot synthesis of β-hydroxyallenamides is reported. This procedure entails chemo- and regioselective hydroboration of 3-en-1-ynyl-sulfonylamides with Cy<sub>2</sub>BH followed by homoallenylation of aldehydes to yield β-hydroxyallenamides (up to 94% yield and >20:1 dr). Controlled synthesis of up to three continuous stereochemical elements was realized. Density functional theory (DFT) calculations suggest a concerted Zimmerman-Traxler chair-like transition state. Initial results sugg ...[more]

PMID: 29861707

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