Scandium‐Bipyridine‐Catalyzed, Enantioselective Alcoholysis of  meso ‐Epoxides | Zendy

Tschöp Andreas | Zendy; Marx Andreas | Zendy; Sreekanth Anakallil R. | Zendy; Schneider Christoph | Zendy

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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)

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