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High Stereoselectivity in One‐Pot Intramolecular Cycloadditions of Olefinic Silyl Nitronates
Author(s) -
Cheng Qian,
Oritani Takayuki,
Horiguchi Tohru,
Shi Qingwen
Publication year - 1999
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/(sici)1099-0690(199910)1999:10<2689::aid-ejoc2689>3.0.co;2-9
Subject(s) - chemistry , silylation , nitronate , stereoselectivity , intramolecular force , cycloaddition , nitro , tetrahydrofuran , olefin fiber , nitrile , medicinal chemistry , stereochemistry , organic chemistry , solvent , catalysis , alkyl
Intramolecular silyl nitronate olefin cycloaddition starting from nitro olefins 1 and leading to substituted tetrahydrofuran rings fused to isoxazolines 5 has been achieved in a one‐pot protocol involving Michael addition, silylation, cycloaddition, and desilylation steps. The results show that unlike nitrile oxides, silyl nitronates undergo highly stereoselective intramolecular cycloadditions to produce functionalized heterocyclic rings.