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Start Over Author "Helaja, Juho" Journal the journal of organic chemistry
8 results on '"Helaja, Juho"'

8. Gold(III)-catalyzed enynamine-cyclopentadiene cycloisomerization with chirality transfer: an experimental and theoretical study indicating involvement of dual Au(III) push-pull assisted cis-trans isomerism

Author

Tom Wirtanen, Mikko Muuronen, Michael Patzschke, Michele Melchionna, Juho Helaja, Wirtanen, Tom, Muuronen, Mikko, Melchionna, Michele, Patzschke, Michael, and Helaja, Juho

Subjects
Cyclopentadiene, 010405 organic chemistry, Stereochemistry, Organic Chemistry, 010402 general chemistry, 01 natural sciences, 0104 chemical sciences, chemistry.chemical_compound, Cycloisomerization, chemistry, Asymmetric carbon, Organic synthesis, Chirality (chemistry), Isomerization, Cis–trans isomerism, Ene reaction
Abstract

A synthetic approach for asymmetric ring-fused cyclopentadienes (Cps) with a chiral carbon at the ring junction has been established from chiral enynamines by achiral Au(III) catalysis. On the basis of experimental and theoretical data, the proposed mechanistic pathway from enynamines to Cps occurs via a Au(III) ene cis–trans isomerization step. Computational studies at DFT and NEVPT2 levels advocate that the cis–trans isomerization step proceeds via a dual Au(III) push–pull assisted intermediate with a low computed rotation barrier. The chirality transfer occurs through a helical-shaped transition state with allenic character. The scope of the catalysis encompasses sterically bulky enynamines including terpene natural products.

Published
2014

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