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Stereo‐Defined Synthetic Route to ( E )‐ and ( Z )‐Tamoxifen Derived from( E )‐1‐Bromo‐2‐iodoalkenes.
Author(s) -
Fujii Yoshino,
Tamura Yuka,
Hashimoto Nako,
Endo Naoki,
Iwasawa Tetsuo
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201900324
Subject(s) - bromine , moiety , chemistry , reagent , olefin fiber , phenol , group (periodic table) , stereochemistry , iodine , combinatorial chemistry , organic chemistry , catalysis
Straightforwardly stereo‐defined syntheses of ( E )‐ and ( Z )‐Tamoxifens were described, including a description of chemo‐selective activation of ( E )‐1‐bromo‐2‐iodoalkenes. The ( E )‐1‐bromo‐2‐iodoalkenes were employed as starting materials; first, the vinylic iodine was transformed into a phenyl group with employing CuTC and PhSnBu 3 reagents. Then the resultant vinylic bromine undertook Suzuki reaction to afford an all‐carbon tetrasubstituted olefin; finally, the phenol‐protective group was converted into the corresponding amino‐moiety. The stereochemistry of the initial ( E )‐1‐bromo‐2‐iodoalkenes was fully retained throughout. Thus, it would provide us a new entry for preparation of Tamoxifens and its related compounds.