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Ring‐Expansion of MCPs in the Presence of DIAD or DEAD and Lewis Acids
Author(s) -
Shao LiXiong,
Shi Min
Publication year - 2004
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.200300515
Subject(s) - diad , chemistry , lewis acids and bases , cyclobutanone , ring (chemistry) , oxygen atom , stereochemistry , medicinal chemistry , organic chemistry , molecule , catalysis , copolymer , polymer
Treatment of methylenecyclopropanes (MCPs) with DIAD or DEAD in MeCN under mild conditions in the presence of Lewis acid Zr(OTf) 4 gave the cyclobutanone ring‐expansion products in good to high yields based on the employed DIAD or DEAD. From a deuterium labeling experiment, the oxygen atom is derived from ambient water. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)