Substrates containing Evan's auxiliary could be used not only for the asymmetric alkylation or aldol reactions, but also for the asymmetric Diels-Alder reaction. Please use your knowledge of the Evan's auxiliarie's to predict the main diastereomer of this reaction. Hint: Et2 AICI acts as a chelating LA here. Me N .. Et₂AICI (2 eq) -78 °C, >99:1 dr (provide stereochemistry) i-Pr

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter14: Elimination
Section: Chapter Questions
Problem 36E
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Substrates containing Evan's auxiliary could be used not only for the asymmetric
alkylation or aldol reactions, but also for the asymmetric Diels-Alder reaction. Please use your
knowledge of the Evan's auxiliarie's to predict the main diastereomer of this reaction. Hint:
Et2 AICI acts as a chelating LA here.
Me
N
..
Et₂AICI (2 eq)
-78 °C, >99:1 dr
(provide stereochemistry)
i-Pr
Transcribed Image Text:Substrates containing Evan's auxiliary could be used not only for the asymmetric alkylation or aldol reactions, but also for the asymmetric Diels-Alder reaction. Please use your knowledge of the Evan's auxiliarie's to predict the main diastereomer of this reaction. Hint: Et2 AICI acts as a chelating LA here. Me N .. Et₂AICI (2 eq) -78 °C, >99:1 dr (provide stereochemistry) i-Pr
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