A convenient method for the synthesis of α-carboxylate ester bromolactones via bromolactonization of alkenoic diesters. Issue 12 (2nd March 2016)

• Record Type: Journal Article
• Authors: Wong, Ying-Chieh; Yeung, Ying-Yeung
• Is Part Of: Organic & biomolecular chemistry. Volume 14:Issue 12(2016)
• Page Start: 3202
• Page End: 3206
• Publication Date: 2016-03-02
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c6ob00311g
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A simple and efficient synthesis of α-ester bromolactones has been developed through the electrophilic bromocyclization of olefinic 1, 3-diesters. Abstract : We developed a simple and efficient method to construct a variety of α-ester bromolactones in good to excellent yields with high diastereoselectivies. The protocol uses readily prepared malonate ester derivatives as substrates, water as an additive and inexpensive N -bromosuccinimide as the halogen source; no catalyst or toxic additive is required. The resulting substituted bromolactones are the fundamental units of many useful molecules.