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Synthesis and Properties of Phospha[5]helicenes Bearing an Inner-Rim Phosphorus Center

Author:
Rahman, Md. Shafiqur, Yoshikai, Naohiko
Source:
Organic letters 2019 v.21 no.9 pp. 3232-3236
ISSN:
1523-7052
Subject:
diastereomers, gold, moieties, optical isomerism, organic compounds, phosphorus, regioselectivity
Abstract:
New phospha[5]helicene derivatives featuring angular fusion of phosphole and carbohelicene moieties have been synthesized using 7-hydroxybenzo[b]phosphole oxide as a key intermediate, which can be regioselectively prepared through one-pot multicomponent coupling. The structural behavior of the present phospha[5]helicene oxide, sulfide, and gold complex in the solid and solution states, along with DFT calculations, demonstrated close correlation between the P-centered chirality and the helical chirality as well as facile helicity inversion and equilibrium between the diastereomers in solution.
Agid:
6397629