(Z)-tamoxifen and tetrasubstituted alkenes and dienes via a regio- and stereospecific three-component magnesium carbometalation palladium(0) cross-coupling strategy.
[reaction: see text] The synthesis of various tetrasubstituted alkenes and dienes in a regio- and stereocontrolled manner is described. This three-component coupling strategy involves the addition of Grignard reagents to propargyl alcohols followed by palladium(0)-mediated cross-coupling with aryl or vinyl halides. This protocol has been applied to the synthesis of (Z)-Tamoxifen and related mimics.
Tessier
Pierre E
PE
Centre for Research in Biopharmaceuticals, Department of Chemistry, University of Ottawa, 10 Marie Curie, Ottawa, Ontario, Canada K1N 6N5.
Penwell
Andrea J
AJ
Souza
Fabio E S
FE
Fallis
Alex G
AG
D000475:Alkenes / Q000138:chemical synthesis*; D016588:Anticarcinogenic Agents / Q000138:chemical synthesis; D008274:Magnesium / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism; D013629:Tamoxifen / Q000031:analogs & derivatives / Q000138:chemical synthesis*
D000475:Alkenes; D016588:Anticarcinogenic Agents; D009942:Organometallic Compounds; D013629:Tamoxifen; D010165:Palladium; D008274:Magnesium