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Cross‐Metathesis Reactions of Homoallyl Methyl Malonates with Sterically Hindered Allylic Esters
Author(s) -
Barile Fabio,
Bassetti Mauro,
D'Annibale Andrea,
Gerometta Renzo,
Palazzi Michele
Publication year - 2011
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.201100916
Subject(s) - chemistry , allylic rearrangement , stereoselectivity , steric effects , geminal , metathesis , selectivity , yield (engineering) , organic chemistry , medicinal chemistry , catalysis , polymerization , polymer , materials science , metallurgy
Abstract The methyl malonate esters of 3‐buten‐1‐ol and 2‐methyl‐3‐buten‐1‐ol can be coupled efficiently to different methallylic esters in the presence of the second‐generation Grubbs catalyst to yield trisubstituted olefins by the cross‐metathesis reaction. Product selectivity and yields depend on the relative amounts of reagents and to a minor extent on the methallylic ester functional group. Alkyl substituents at either the allylic or the geminal positions significantly affect the product yields and the E / Z stereoselectivity.