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Iodolactonization: Synthesis, Stereocontrol, and Compatibility Studies

2011; Wiley; Volume: 2012; Issue: 1 Linguagem: Inglês

10.1002/ejoc.201101343

1434-193X

Martins S. Oderinde, Howard N. Hunter, Stacy W. Bremner, Michael G. Organ,

Synthetic Organic Chemistry Methods

Abstract Generalized iodolactonization conditions have been developed for the formation of both cis ‐ and trans ‐γ‐lactones from 3‐pentenoic acid derivatives containing various protected alcohol moieties. Kinetic control of the reaction using iodine and base at 0 °C for 6 h provided the cis ‐lactone with good selectivity (75:25), and thermodynamic control at room temperature for 24 h provided the trans ‐lactone with excellent selectivity (98:2).