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DIANANE‐Cr III ‐salen Complexes as Highly Enantioselective Catalysts for Hetero‐Diels–Alder Reactions of Aldehydes with Dienes
Author(s) -
Berkessel Albrecht,
Vogl Nadine
Publication year - 2006
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.200600359
Subject(s) - chemistry , diene , enantioselective synthesis , chromium , catalysis , reactivity (psychology) , benzaldehyde , diels–alder reaction , pyran , organic chemistry , medicinal chemistry , medicine , natural rubber , alternative medicine , pathology
A new type of chromium‐salen complex bearing DIANANE ( endo , endo ‐2,5‐diaminonorbornane) as chiral backbone has been synthesized and applied to the hetero‐Diels–Alder reaction of Danishefsky’s diene with various aldehydes. The reactions afford the corresponding 2‐substituted 2,3‐dihydro‐4 H ‐pyran‐4‐ones in high yields and enantioselectivities (up to 96 % ee ). The effect of different counteranions of the complex on reactivity as well as enantioselectivity has been investigated. Besides Danishefsky’s diene, reaction of the less reactive 1‐methoxybutadiene with benzaldehyde and ethyl glyoxylate can be effected by the chromium catalysts as well.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)