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From Axial Chirality to Central Chiralities: Pinacol Cyclization of 2,2′‐Biaryldicarbaldehyde to trans ‐9,10‐Dihydrophenanthrene‐9,10‐diol
Author(s) -
Ohmori Ken,
Kitamura Mitsuru,
Suzuki Keisuke
Publication year - 1999
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(19990503)38:9<1226::aid-anie1226>3.0.co;2-t
Subject(s) - pinacol , chirality (physics) , stereochemistry , diol , chemistry , physics , organic chemistry , chiral symmetry , catalysis , particle physics , nambu–jona lasinio model , quark
Two salient features —the stereoselectivity to give only the trans ‐diol, and the stereospecificity to transmit the axial chirality (in case the starting biphenyl is configurationally stable) onto two stereogenic centers of the product—characterize the pinacol cyclization of 2,2′‐biaryldicarbaldehydes (see reaction). The accessibility of trans ‐9,10‐dihydrophenanthrene‐9,10‐diols provides the new enantiopure C 2 ‐symmetric diol 1 , which shows potential utility in asymmetric synthesis.