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Scandium‐Bipyridine‐Catalyzed, Enantioselective Alcoholysis of meso ‐Epoxides
Author(s) -
Tschöp Andreas,
Marx Andreas,
Sreekanth Anakallil R.,
Schneider Christoph
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200601101
Subject(s) - chemistry , scandium , enantioselective synthesis , catalysis , bipyridine , yield (engineering) , ring (chemistry) , diol , epoxide , organic chemistry , medicinal chemistry , crystal structure , materials science , metallurgy
The scandium‐bipyridine‐catalyzed ring‐opening of meso ‐epoxides with aliphatic alcohols has been studied. Aromatic epoxides were ring‐opened with >90 % ee furnishing valuable 1,2‐diol monoethers in typically good yields whereas aliphatic epoxides gave rise to moderate enantioselectivities. The catalyst loading may be lowered to 2–5 mol‐% with only marginal effects on yield and enantioselectivity. A strong positive non‐linear effect was observed pointing to aggregation phenomena of the chiral catalyst.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)