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Enantioselective Synthesis of Ferrocene‐ or Cymantrene‐Fused Planar‐Chiral Phospholes
Author(s) -
Hu Hao,
Wu WeiYi,
Takahashi Tamotsu,
Yoshida Kazuhiro,
Ogasawara Masamichi
Publication year - 2017
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.201600875
Subject(s) - chemistry , enantioselective synthesis , ferrocene , phosphole , planar chirality , chirality (physics) , acetal , stereochemistry , yield (engineering) , organic chemistry , catalysis , chiral anomaly , electrochemistry , nambu–jona lasinio model , physics , materials science , electrode , fermion , quantum mechanics , metallurgy
Planar‐chiral ferrocene‐fused phosphole ( S )‐ 1a was prepared in an enantiomerically pure form by enantioselective transformation. The synthesis was started with Kagan's chiral ferrocenyl acetal (–)‐ 2a , and bromo and ( Z )‐2‐bromovinyl substituents were introduced at the 1‐ and 2‐positions of the ferrocene platform in ( S )‐ 6a with controlling its planar chirality. The double Li/Br exchange on ( S )‐ 6a followed by the reaction with PhPBr 2 provided ( S )‐ 1a in excellent yield. The structure of ( S )‐ 1a was determined by X‐ray crystallography. Planar‐chiral cymantrene‐fused phosphole ( S )‐ 1b was also prepared by an analogous asymmetric transformation starting with Jaouen's chiral cymantrenyl acetal (+)‐ 2b .