Synthesis of planar-chiral paracyclophanes via samarium(II)-catalyzed intramolecular pinacol coupling

Tsuyoshi Ueda; Nobuhiro Kanomata; Hajime Machida

doi:10.1021/ol0506258

Synthesis of planar-chiral paracyclophanes via samarium(II)-catalyzed intramolecular pinacol coupling

Tsuyoshi Ueda, Nobuhiro Kanomata, Hajime Machida

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58 Citations (Scopus)

Abstract

(Chemical Equation Presented) A series of [n]jparacyclophanediols (n = 8-12) was synthesized by samarium-catalyzed pinacol coupling for their ansa-bridge formation. Enantiomerically pure [n]jparacyclophane esters were derived from the diols in a several steps via chiral resolution (for n = 10) or via crystallization-induced asymmetric transformation (for n = 11) by using amino alcohol auxiliaries and their selective cleavages.

Original language	English
Pages (from-to)	2365-2368
Number of pages	4
Journal	Organic Letters
Volume	7
Issue number	12
DOIs	https://doi.org/10.1021/ol0506258
Publication status	Published - 2005 Jun 9

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Molecular Medicine

Cite this

Ueda, T., Kanomata, N., & Machida, H. (2005). Synthesis of planar-chiral paracyclophanes via samarium(II)-catalyzed intramolecular pinacol coupling. Organic Letters, 7(12), 2365-2368. https://doi.org/10.1021/ol0506258

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AB - (Chemical Equation Presented) A series of [n]jparacyclophanediols (n = 8-12) was synthesized by samarium-catalyzed pinacol coupling for their ansa-bridge formation. Enantiomerically pure [n]jparacyclophane esters were derived from the diols in a several steps via chiral resolution (for n = 10) or via crystallization-induced asymmetric transformation (for n = 11) by using amino alcohol auxiliaries and their selective cleavages.

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10.1021/ol0506258