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The Catalytic Asymmetric Diels–Alder Reactions and Post-cycloaddition Reductive Transpositions of 1-Hydrazinodienes

✍ Scribed by Dr. Hao Xie; Dr. Glenn M. Sammis; Dr. Eric M. Flamme; Christina M. Kraml; Prof. Dr. Erik J. Sorensen

Publisher: John Wiley and Sons
Year: 2011
Tongue: English
Weight: 245 KB
Volume: 17
Category: Article
ISSN: 0947-6539
DOI: 10.1002/chem.201102394

No coin nor oath required. For personal study only.

✦ Synopsis

Scheme 1. A cyclohexene synthesis featuring a post-cycloaddition reductive transposition. Scheme 2. The Diels-Alder and reductive transposition chemistry of a 1hydrazinodiene. Reaction conditions: a) diethylmaleate, Et 2 AlCl, 23 8C, 75 %; b) Pd 2 A C H T U N G T R E N N U N G (dba) 3 , Et 2 NH, THF, 23 8C; c) NaOAc, MeOH, 49 % over two steps; Alloc: allyloxycarbonyl.

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