- Stereochemistries of geometric isomers of 4 (2 bromo 1,2 diphenylvinyl)phenol, 4 (2 bromo 1,2 diphenylvinyl)anisole, and 2 [p (2 bromo 1,2 diphenylvinyl)phenoxy]triethylamine: corrections of the literature
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The stereochemistries of geometric isomers of 4 (2 bromo 1,2 diphenylvinyl) phenol, 4 (2 bromo 1,2 diphenylvinyl) anisole, and 2 [p (2 bromo 1,2 diphenylvinyl) phenoxy] triethylamine were determined by conversion of the phenolic analog to the ethers and subsequent comparison of physical properties with those of 2 [p (2 chloro 1,2 diphenylvinyl) phenoxy] triethylamine of known stereochemistry.
- Richardson Jr.,Benson,Hite
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- Trans-stilbene as a starting material for the synthesis of tamoxifen based on palladium-catalyzed cross-coupling reactions
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(Z)-Tamoxifen was synthesized from a simple olefin (trans-stilbene) in 5 steps and 40% overall yield (Z/E = 74:26). The phenyl substituted group (4-Me2NCH2CH2OC6H4) was attached by a bromination-dehydrobromination-Suzuki reaction sequence. Subsequently, the ethyl group was attached to the triarylated olefin by a bromination-Negishi reaction sequence. Both the Suzuki and Negishi cross-coupling processes are stereospecific, and the stereo-selectivity depends only on the bromination-dehydrobromination reactions. (Z)-Tamoxifen was also obtained from trans-stilbene in only 3 steps by using Heck reaction-bromination- Negishi reaction sequence in 57% overall yield (Z/E = 65:35). Georg Thieme Verlag Stuttgart.
- Nunes, Carolina M.,Limberger, Jones,Poersch, Silvia,Seferin, Marcus,Monteiro, Adriano L.
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scheme or table
p. 2761 - 2765
(2010/01/21)
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