Premium
Efficient Generation of ortho ‐Naphthoquinone Methides from 1,4‐Epoxy‐1,4‐dihydronaphthalenes and Their Annulation with Allyl Silanes
Author(s) -
Sawama Yoshinari,
Shishido Yuko,
Yanase Takayoshi,
Kawamoto Koichi,
Goto Ryota,
Monguchi Yasunari,
Kita Yasuyuki,
Sajiki Hironao
Publication year - 2013
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.201207315
Subject(s) - silanes , annulation , trimethylsilyl , stereoselectivity , 1,4 naphthoquinone , naphthoquinone , chemistry , organic chemistry , computer science , catalysis , silane
Pharmaceutically useful dihydronaphthopyran derivatives were obtained in good yield by the regio‐ and stereoselective annulation of ortho ‐naphthoquinone methides with allyl silanes. The ortho ‐naphthoquinone methides were generated in situ from 1‐siloxymethyl‐1,4‐epoxy‐1,4‐dihydronaphthalenes under FeCl 3 catalysis (see scheme; allyl‐TMS=allyltrimethylsilane, TBS= tert ‐butyldimethylsilyl, TMS=trimethylsilyl).