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Synthesis of 3,4‐Dimethylidene Oxacycles through Prins‐Type Cyclization of Allenylmethylsilanes
Author(s) -
Ullapu Punna Reddy,
Kim Young Seub,
Lee Jae Kyun,
Pae Ae Nim,
Kim Youseung,
Min SunJoon,
Cho Yong Seo
Publication year - 2011
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201100162
Subject(s) - prins reaction , tetrahydrofuran , stereoselectivity , silanes , ring (chemistry) , type (biology) , chemistry , stereochemistry , organic chemistry , catalysis , silane , solvent , ecology , biology
An efficient synthesis of 3,4‐dimethylidene oxacycles including oxolanes and oxepanes through Prins‐type cyclization of hydroxy(allenylmethyl)silanes is described. We have shown that 2‐substituted tetrahydrofuran derivatives could be produced by using this strategy although the 5‐ endo ‐trig cyclization mode is stereoelectronically disfavored. We also applied our method to the stereoselective synthesis of 2,7‐ cis ‐3,4‐dimethylidene oxepanes, which were used for constructing more complex ring systems, such as polyether bicycles or tricycles.