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Enantioselective Synthesis of 2,3‐Dihydrofurans via Ammonium Ylides
Author(s) -
Worgull Dennis,
Öhler Laura,
Strache Joss Pepe,
Friedrichs Teresa,
Ullrich Patrick
Publication year - 2017
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.201701176
Subject(s) - chemistry , ylide , enantioselective synthesis , ammonium , yield (engineering) , salt (chemistry) , amine gas treating , organic chemistry , catalysis , materials science , metallurgy
A chiral, ammonium ylide based access to tetrasubstituted 2,3‐dihydrofurans starting from readily available benzylidene dicarbonyls and bromo acetophenones has been developed. The products are obtained in moderate to good yields with excellent diasteroselectivity and good to excellent enantioselectivity (up to 99:1 e.r.). The employed chiral amine can be recovered in near quantitative yield. The transformation can be run as a three‐component one‐pot reaction, generating the ammonium salt and ylide in situ. The scope of this reaction includes 17 new dihydrofurans with aromatic or heteroaromatic substituents.