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Convenient Approach to 2‐Substituted (Thio)morpholin‐3‐ones from α‐Diazoacetates via X‐H Carbene Insertion – Lactamization Sequence
Author(s) -
Solovyov Igor,
Dar'in Dmitry,
Krasavin Mikhail
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201901238
Subject(s) - thio , carbene , chemistry , sequence (biology) , medicinal chemistry , insertion reaction , stereochemistry , combinatorial chemistry , catalysis , organic chemistry , biochemistry
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 Rh 2 (esp) 2 ‐catalyzed X‐H insertion reaction, Boc group removal and ambient‐temperature lactamization and is conveniently conducted in one‐pot format.