Enantioselective copper catalysed intramolecular C–H insertion reactions of α-diazo-β-keto sulfones, α-diazo-β-keto phosphine oxides and 2-diazo-1, 3-diketones; the influence of the carbene substituent. Issue 12 (7th March 2017)

• Record Type: Journal Article
• Authors: Shiely, Amy E.; Slattery, Catherine N.; Ford, Alan; Eccles, Kevin S.; Lawrence, Simon E.; Maguire, Anita R.
• Is Part Of: Organic & biomolecular chemistry. Volume 15:Issue 12(2017)
• Page Start: 2609
• Page End: 2628
• Publication Date: 2017-03-07
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c7ob00214a
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Enantioselective C–H insertion reactions are described. Abstract : Enantioselectivities in C–H insertion reactions, employing the copper-bis(oxazoline)-NaBARF catalyst system, leading to cyclopentanones are highest with sulfonyl substituents on the carbene carbon, and furthermore, the impact is enhanced by increased steric demand on the sulfonyl substituent (up to 91%ee). Enantioselective intramolecular C–H insertion reactions of α-diazo-β-keto phosphine oxides and 2-diazo-1, 3-diketones are reported for the first time.