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Rhodium-catalyzed Asymmetric Ring-opening Reactions of N-Boc-azabenzonorbornadiene with N-Substituted Piperazine Nucleophiles

✍ Scribed by Yuhua Wu; Dingqiao Yang; Heping Zeng; Lei Xie; Lihuan Wu; Haihong Mo; Xiongjun Zuo

Publisher
John Wiley and Sons
Year
2010
Tongue
English
Weight
133 KB
Volume
28
Category
Article
ISSN
0256-7660

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✦ Synopsis

Abstract

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.

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