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Anionic Cascade Routes to Sulfur and Nitrogen Heterocycles Originating from Thio‐ and Aminophosphate Precursors
Author(s) -
Das Pradipta,
Njardarson Jon T.
Publication year - 2016
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.201600312
Subject(s) - chemistry , alkoxide , intramolecular force , nucleophile , sulfur , heteroatom , thio , nitrogen , sn2 reaction , carbanion , leaving group , alcohol , organic chemistry , catalysis , ring (chemistry)
This micro‐review attempts to comprehensively cover reported reactions employing thio‐ and aminophosphate precursors for forming sulfur and nitrogen heterocycles. All such reactions are triggered by initial formation of an alkoxide, most commonly by attack of a carbon or heteroatom nucleophile onto a carbonyl group. The alkoxide intermediate facilitates an intramolecular transfer of the phosphate group to form a thiolate or nitrogen atom anion, which then terminate the anionic cascade via an intramolecular O‐phosphate displacement reaction to form the heterocyclic products.