118964-06-0Relevant articles and documents
Enantiomerically Enriched α-Borylzinc Reagents by Nickel-Catalyzed Carbozincation of Vinylboronic Esters
Zhang, Chenlong,Hu, Weipeng,Lovinger, Gabriel J.,Jin, Jing,Chen, Jingjia,Morken, James P.
, p. 14189 - 14195 (2021/09/11)
In this paper is described a synthesis of enantiomerically enriched, configurationally stable organozinc reagents by catalytic enantioselective carbozincation of a vinylboronic ester. This process furnishes enantiomerically enriched α-borylzinc intermediates that are shown to undergo stereospecific reactions, producing enantioenriched secondary boronic ester products. The properties of the intermediate α-borylzinc reagent are probed and the synthetic utility of the products is demonstrated by application to the synthesis of (-)-aphanorphine and (-)-enterolactone.
An effective route to (-)-aphanorphine using D-tyrosine as a chiral building block
Li, Min,Zhou, Peijie,Roth, Hans F.
, p. 55 - 60 (2007/12/31)
A stereoselective approach toward a naturally occurring alkaloid, (-)-aphanorphine, has been achieved via a series of reactions from Boc-D-tyrosine. Georg Thieme Verlag Stuttgart.
Synthesis of (-)-aphanorphine using aryl radical cyclization.
Tamura,Yanagimachi,Kobayashi,Ishibashi
, p. 2427 - 2429 (2007/10/03)
[structure: see text] The synthesis of (-)-aphanorphine was achieved by using Bu(3)SnH-mediated aryl radical cyclization of 1-benzyloxycarbonyl-2-(2-bromo-4-methoxyphenylmethyl)-2-methoxycarbonyl-4-(phenylthiomethylene)pyrrolidine, leading to exclusive fo