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Rhodium‐catalyzed Asymmetric Ring‐opening Reactions of N ‐Boc‐azabenzonorbornadiene with N ‐Substituted Piperazine Nucleophiles
Author(s) -
Wu Yuhua,
Yang Dingqiao,
Zeng Heping,
Xie Lei,
Wu Lihuan,
Mo Haihong,
Zuo Xiongjun
Publication year - 2010
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201090059
Subject(s) - chemistry , piperazine , nucleophile , enantiomer , medicinal chemistry , ring (chemistry) , catalysis , ligand (biochemistry) , diamine , rhodium , enantiomeric excess , stereochemistry , enantioselective synthesis , organic chemistry , receptor , biochemistry
Asymmetric ring‐opening reactions of N ‐Boc‐azabenzonorbornadiene with N ‐substituted piperazine nucleophiles in the presence of 5 mol% of [Rh(COD)Cl] 2 and 10 mol% of chiral ligand, ( R , S )‐PPF‐P‐ t ‐Bu 2 , gave the corresponding 1,2‐diamine product in moderate to excellent yields (up to 95%) with reasonable enantiomeric excesses (up to 70% ee ). The results showed that the nature of ligands had significant influence on the yields and the enantiomeric excesses.