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Synthesis of Eight‐Membered Lactones: Intermolecular [6+2] Cyclization of Amphoteric Molecules with Siloxy Alkynes
Author(s) -
Zhao Wanxiang,
Wang Zhaobin,
Sun Jianwei
Publication year - 2012
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201200513
Subject(s) - alkynes , cyclization , homogeneous catalysis , lactones , medium ring compounds
That's about the size of it : The title molecules react with siloxy alkynes in the presence of a Brønsted acid to deliver medium‐sized lactones through a [6+2] cyclization (see scheme; TIPS=triisopropylsilyl). This process is the first intermolecular synthesis of such lactones and involves a sequence of several selective ring‐opening/ring‐closing events.