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 |
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Pages (from-to) | 2365-2368 |
Number of pages | 4 |
Journal | Organic Letters |
Volume | 7 |
Issue number | 12 |
DOIs | |
Publication status | Published - 2005 Jun 9 |
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ASJC Scopus subject areas
- Molecular Medicine
Cite this
Synthesis of planar-chiral paracyclophanes via samarium(II)-catalyzed intramolecular pinacol coupling. / Ueda, Tsuyoshi; Kanomata, Nobuhiro; Machida, Hajime.
In: Organic Letters, Vol. 7, No. 12, 09.06.2005, p. 2365-2368.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Synthesis of planar-chiral paracyclophanes via samarium(II)-catalyzed intramolecular pinacol coupling
AU - Ueda, Tsuyoshi
AU - Kanomata, Nobuhiro
AU - Machida, Hajime
PY - 2005/6/9
Y1 - 2005/6/9
N2 - (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.
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.
UR - http://www.scopus.com/inward/record.url?scp=20544442024&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=20544442024&partnerID=8YFLogxK
U2 - 10.1021/ol0506258
DO - 10.1021/ol0506258
M3 - Article
C2 - 15932199
AN - SCOPUS:20544442024
VL - 7
SP - 2365
EP - 2368
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 12
ER -