Facile reductive oxy-Nazarov cyclization of 2-methoxy-2, 4-hexadienoates. Issue 3 (18th January 2017)

• Record Type: Journal Article
• Authors: Chen, Yang; Li, Wei-Dong Z.
• Is Part Of: Tetrahedron letters. Volume 58:Issue 3(2017)
• Page Start: 248
• Page End: 251
• Publication Date: 2017-01-18
• Subjects: Reduction -- Dibal-H -- Oxy-Nazarov -- 5-Hydroxyl cyclopentenone; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.12.020
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: A facile method for synthesis of 5-hydroxyl cyclopentenone derivatives was reported. This transformation represents a new variant of the iso-Nazarov cyclization. The approach has great potential application in natural product synthesis. Abstract: Reduction of 2-methoxy-2, 4-hexadienoates with Dibal-H in toluene at −78 °C resulted in a facile formation of 5-hydroxyl cyclopentenone derivatives. This novel transformation was proposed as a variant of the oxy-Nazarov cyclization of the corresponding 2-methoxy aldehyde intermediate via the cationic Al-chelate as depicted in Fig. 2a.