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Copper‐Mediated and ‐Catalyzed o ‐DPPB‐Directed Allylic Substitution
Author(s) -
Breit Bernhard,
Demel Peter
Publication year - 2001
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 - 10.1002/1615-4169(200107)343:5<429::aid-adsc429>3.0.co;2-k
Subject(s) - chemistry , allylic rearrangement , reagent , stereoselectivity , leaving group , copper , chirality (physics) , substitution (logic) , nucleophilic substitution , substitution reaction , nucleophile , medicinal chemistry , combinatorial chemistry , catalysis , stereochemistry , organic chemistry , chiral symmetry breaking , physics , quantum mechanics , computer science , nambu–jona lasinio model , programming language , quark
Complete control of chemo‐, regio‐ and stereoselectivity in the course of copper‐catalyzed and ‐mediated allylic substitution could be obtained with the ortho ‐diphenylphosphanyl ( o ‐DPPB) function as a reagent‐directing leaving group. Complete chirality transfer by way of a syn ‐addition process has been achieved for cyclic and acyclic systems. Readily available Grignard reagents may be employed as nucleophiles and the directing o ‐DPPB group can be recovered quantitatively. The reaction requires neither cooling nor an excess of organometallic reagent.