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Domino Heck–Diels–Alder Reactions of Differently Substituted Cyclopropylallenes
Author(s) -
Knoke Mario,
de Meijere Armin
Publication year - 2005
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.200500024
Subject(s) - chemistry , domino , cycloaddition , diastereomer , cyclohexene , aryl , yield (engineering) , heck reaction , cyanine , ring (chemistry) , medicinal chemistry , diels–alder reaction , organic chemistry , catalysis , fluorescence , alkyl , materials science , physics , quantum mechanics , metallurgy
Several substituted cyclopropylallenes were coupled under Heck conditions with aryl iodides and aryl bromides, respectively, and the 1,3,5‐hexatrienes resulting with ring‐opening of the cyclopropyl group, were captured in situ by a number of reactive dienophiles to yield oligosubstituted cyclohexene derivatives (8–86 %, 33 examples) with diastereomeric ratios ranging from 1.4:1 to 4.9:1. The influences of the number, the nature and the pattern of substituents have been elaborated. The [4+2] cycloaddition most probably proceeds in two steps through a mesomerically well stabilized 1,6‐zwitterionic intermediate. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)