Design and Synthesis of Planar Chiral Heterocyclic Carbene Precursors Derived from [2.2]Paracyclophane

A unique family of planar chiral symmetrical N-heterocyclic carbene precursors with restricted flexibility derived from [2.2]paracyclopane were obtained by a new synthetic route. The resolution of 4-amino-13-bromo[2.2]paracyclophane was achieved with relatively high efficiency. Starting from (4S p,1...

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Bibliographic Details
Published in:Journal of organic chemistry 2008-06, Vol.73 (11), p.4330-4333
Main Authors: Duan, Wenzeng, Ma, Yudao, Xia, Houqi, Liu, Xueying, Ma, Qingshuang, Sun, Junshan
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Organic chemistry
Preparations and properties
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Summary:A unique family of planar chiral symmetrical N-heterocyclic carbene precursors with restricted flexibility derived from [2.2]paracyclopane were obtained by a new synthetic route. The resolution of 4-amino-13-bromo[2.2]paracyclophane was achieved with relatively high efficiency. Starting from (4S p,13R p)-4-amino-13-bromo[2.2]paracyclophane, the planar chiral pseudogem-disubstituted [2.2]paracyclophanyl dihydroimidazoliums were prepared in a four-step sequence with good yields. The resulting dihydroimidazolium salts were fully characterized with a series of methods including single-crystal X-ray diffraction technique.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo800468x