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Chirality transfer in palladium catalyzed reactions of allylammonium salts

✍ Scribed by Takayuki Doi; Arata Yanagisawa; Masahiro Miyazawa; Keiji Yamamoto

Book ID: 103977086
Publisher: Elsevier Science
Year: 1995
Tongue: English
Weight: 254 KB
Volume: 6
Category: Article
ISSN: 0957-4166
DOI: 10.1016/0957-4166(95)00021-g

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✦ Synopsis

Optically active 1-isobutyl-2(Z)-butenyltrimethylammonium iodide (10) underwent allylation with dimethyl sodiomalonate in the presence of a palladium(O) catalyst. The reaction proceeded predominantly with 1,3 transposition and with inversion of configuration due probably to a prior isomerization from anti to syn-cr-allylpalladium intermediate (14--915). The stereochemistry observed in the reaction with phenylzinc chloride was opposite to that with the soft nucleophile.

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