Work

Enantioselective Alkyne-Mediated Aldehyde Allylation of Alcohol Proelectrophiles Using RuHCl(CO)(PPh 3 ) 3 as Precatalyst

Year: 2025

Type: article

Abstract: The catalyst assembled from inexpensive RuHCl(CO)(PPh 3 ) 3, JOSIPHOS (SL-J009-1), and either NaI or KI affects anti -diastereo- and enantioselective alkyne-mediated allylation of alcohol proelectrophiles via hydrogen autotransfer. This protocol offers an alternative to the iodide-bound precatalyst RuI(CO) 3 (η 3 -C 3 H 5 ), which is somewhat sensitive and not commercially available. Application to the asymmetric synthesis of cis -2,3-disubstituted pyrrolidines 5a – 5c and cis -2,3-disubstituted azetidine 6 is described.

Source: Organic Letters

DOI: 10.1021/acs.orglett.5c04678

Authors: Madeline M. Evarts, Thien-Quang N. Nguyen, Michael J. Krische

Institution: The University of Texas at Austin

Language: English

Topic: Asymmetric Hydrogenation and Catalysis

Subfield: Inorganic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: Welch Foundation, National Institute of General Medical Sciences

Awards: G3277079756, G7991472476