Convenient Approach to 2‐Substituted (Thio)morpholin‐3‐ones from α‐Diazoacetates via X‐H Carbene Insertion – Lactamization Sequence. Issue 45 (18th November 2019)

• Record Type: Journal Article
• Authors: Solovyov, Igor; Dar'in, Dmitry; Krasavin, Mikhail
• Is Part Of: European journal of organic chemistry. Issue 45(2019)
• Page Start: 7432
• Page End: 7438
• Publication Date: 2019-11-18
• Subjects: Diazo compounds -- Diazo transfer -- Homogeneous catalysis -- Insertion -- Lactamization; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201901238
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : Stepwise coupling of N ‐Boc‐protected β‐aminoethanols or β‐mercaptoethylamines with various α‐diazoacetates provides a new, unified approach to constructing (thio)morpholin‐3‐ones. The process involves a Rh2 (esp)2 ‐catalyzed X‐H insertion reaction, Boc group removal and ambient‐temperature lactamization and is conveniently conducted in one‐pot format. Abstract : Substituted α‐diazo acetates are coupled with N ‐Boc‐protected β‐aminoethanols or β‐mercaptoethylamines to give medicinally important (thio)morpholin‐3‐ones.