Stereo- and Site-Selective Crotylation of Alcohol Proelectrophiles Via Ruthenium-Catalyzed Hydrogen Auto-Transfer Mediated by Methylallene and Butadiene

Overview

Journal Angew Chem Int Ed Engl

Specialty Chemistry

Date 2022 Oct 6

PMID 36201364

Authors

Eliezer Ortiz

Brian J Spinello

Yoon Cho

Jessica Wu

Michael J Krische

Affiliations

Soon will be listed here.

Abstract

Iodide-bound ruthenium-JOSIPHOS complexes catalyze the redox-neutral C-C coupling of primary alcohols with methylallene (1,2-butadiene) or 1,3-butadiene to form products of anti-crotylation with good to excellent levels of diastereo- and enantioselectivity. Distinct from other methods, direct crotylation of primary alcohols in the presence of unprotected secondary alcohols is possible, enabling generation of spirastrellolide B (C9-C15) and leucascandrolide A (C9-C15) substructures in significantly fewer steps than previously possible.

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