The Orthoester Johnson–Claisen Rearrangement in the Synthesis of Bioactive Molecules, Natural Products, and Synthetic Intermediates – Recent Advances1. Issue 14 (29th October 2013)

• Record Type: Journal Article
• Authors: Fernandes, Rodney A.; Chowdhury, Asim K.; Kattanguru, Pullaiah
• Is Part Of: European journal of organic chemistry. Issue 14(2014)
• Page Start: 2833
• Page End: 2871
• Publication Date: 2013-10-29
• Subjects: Synthetic methods -- Rearrangement -- Natural products -- Stereoselectivity -- Building blocks; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201301033
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: The orthoester Johnson–Claisen rearrangement, an important C–C bond forming reaction, has been used enormously in the past four decades in the synthesis of bioactive molecules, natural products, synthetic intermediates, analogues, and useful building blocks. The method has also featured in chemical modification of materials. This review covers developments in this rearrangement since 2003. Unlike many other forms of Claisen rearrangement, this reaction is generally a one‐pot, one‐step process. It is compatible with numerous functional groups, despite its use of acid catalysis, and offers chirality transfer to produce stereoselective products. The method also offers opportunities for rapid modifications to various functionalized compounds and building blocks for further synthetic exploration. Abstract : The orthoester Johnson–Claisen rearrangement is a one‐pot, one‐step process for C–C bond formation. This review covers developments in the orthoester Johnson–Claisen rearrangement since 2003. The applications of this rearrangement in the synthesis of bioactive molecules, natural products, analogues, synthetic intermediates, and building blocks are covered.