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Naplephos through the Looking‐Glass: Chiral Bis(phosphanylamides) Based on β‐1,2‐ D ‐Glucodiamine and Their Application in Enantioselective Allylic Substitutions
Author(s) -
Benessere Vincenzo,
De Roma Antonella,
Del Litto Raffaella,
Lega Matteo,
Ruffo Francesco
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100960
Subject(s) - desymmetrization , enantioselective synthesis , chemistry , enantiomer , allylic rearrangement , stereochemistry , catalysis , organic chemistry
The straightforward design of a new library of chiral ligands (elpanphos) based on β‐1,2‐ D ‐glucodiamine is described, which represents the enantiomeric counterpart of the naplephos library. In this guise, two representative ligands have been successfully applied in the Pd‐catalyzed desymmetrization of meso ‐cyclopent‐2‐ene‐1,4‐diol, which leads to the expected enantiomer within short times and with high ee s in both traditional and unconventional solvents.