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Remarkable Electronic Effect on the Diastereoselectivity of the Heck Reaction of Methyl Cinnamate with Arenediazonium Salts: Formal Total Synthesis of (±)‐Indatraline and (±)‐Sertraline
Author(s) -
Pastre Julio Cezar,
Correia Carlos Roque Duarte
Publication year - 2009
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200900032
Subject(s) - chemistry , heck reaction , electrophile , stereoselectivity , ligand (biochemistry) , combinatorial chemistry , organic chemistry , palladium , catalysis , biochemistry , receptor
AbstractAn efficient and stereoselective protocol for the preparation of β,β‐disubstituted acrylates in good to high yields by means of a Heck–Matsuda arylation was accomplished. The method employs a base‐ and ligand‐free Heck arylation reaction of methyl cinnamate using both electron‐deficient and electron‐rich arenediazonium salts as electrophiles. The Heck reaction displays a remarkable electronic dependence regarding the diastereoselectivity of the arylation process, which correlates with the electronic nature of the arenediazonium salts employed. A rationale for the observed diastereoselectivity is presented. The overall methodology provides a convenient route to 3‐arylindanones and 4‐aryltetralones allowing the concise formal total syntheses of the therapeutically important psychoactive compounds (±)‐indatraline and (±)‐sertraline.