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Efficient Synthesis of Methylenetetrahydrofurans and Methylenepyrrolidines by Formal [3+2] Cycloadditions of Propargyl Substrates
Author(s) -
Yamazaki Shoko
Publication year - 2008
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200800195
Subject(s) - allylic rearrangement , propargyl , electrophile , lewis acids and bases , chemistry , formal synthesis , ring (chemistry) , base (topology) , combinatorial chemistry , organic chemistry , catalysis , mathematics , mathematical analysis
Recent developments concerning the synthesis of methylenetetrahydrofurans and methylenepyrrolidines by one‐pot formal [3+2] cycloadditions involving propargylic (and allylic) alcohols and amines with electrophilic alkenes are described. The synthetic methods provide powerful tools to prepare highly functionalized oxygen‐ and nitrogen‐containing five‐membered ring systems. The reactions can be effectively promoted by base, base/transition metals, and Lewis acids, depending on the substrates.