96212-86-1Relevant articles and documents
Process development for a large scale stereoselective synthesis of (Z)-(1-bromobut-1-ene-1,2-diyl)dibenzene, a key intermediate of a selective estrogen receptor modulator
Cann, Reginald O.,Waltermire, Robert E.,Chung, Jihchin,Oberholzer, Matthew,Kasparec, Jiri,Ye, Yun K.,Wethman, Robert
experimental part, p. 1147 - 1152 (2011/04/16)
Two efficient large scale syntheses of (Z)-(1-bromobut-1-ene-1,2-diyl) dibenzene are described. The first is a three-step synthetic sequence from trimethyl(phenylethynyl)silane in 63% overall yield. The key transformations involved the stereospecific carb
Carbolithiation of diphenylacetylene as a stereoselective route to (Z)-tamoxifen and related tetrasubstituted olefins
McKinley, Neola F.,O'Shea, Donal F.
, p. 9552 - 9555 (2007/10/03)
(Chemical Equation Presented) Carbolithiation of diphenylacetylene can be exploited to generate (E)-1-lithio-1,2-diphenylalkyl-1-enes which can be reacted in situ with triisopropylborate to stereoselectively provide (E)-1,2-diphenyl-1-alkylene boronic acids. These tetrasubstituted vinylboronic acids served as versatile intermediates for the generation of tetrasubstituted olefins with retention of stereochemistry. The application of this method for the stereoselective synthesis of (Z)-tamoxifen and related analogues is described.
Highly Stereoselective Access to an (E)-Vinyl Bromide from an Aryl Ketone Leads to Short Syntheses of (Z)-Tamoxifen and Important Substituted Derivatives
Potter, Gerard A.,McCague, Raymond
, p. 6184 - 6187 (2007/10/02)
The enol triflate derived from a 1-(4-alkoxyphenyl)-2-phenyl-1-butanone is unstable, fragmenting to a vinyl cation that can be trapped by bromide ion.The E isomer of the vinyl bromide which is formed in preference (20:1) gave, upon palladium-catalyzed cou
Stereospecific Synthesis of (Z)-Tamoxifen via Carbometalation of Alkynylsilanes
Miller, R. Bryan,Al-Hassan, Mohammed I.
, p. 2121 - 2123 (2007/10/02)
A sterospecific synthesis of (Z)-tamoxifen, a tetrasubstituted alkene with antiestrogenic activity, is described.The key reaction that establishes the olefin stereochemistry is a carbometalation of phenyl(trimethylsilyl)acetylene with diethylaluminum chloride-titanocene dichloride.A key intermediate that would lead to (E)-tamoxifen was also prepared in an analogous stereospecific manner.