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  • Asymmetric synthesis of (-)-aurantioclavine via palladium-catalyzed intramolecular allylic amination.

Asymmetric synthesis of (-)-aurantioclavine via palladium-catalyzed intramolecular allylic amination.

Organic letters (2014-01-28)
Satoshi Suetsugu, Hiromi Nishiguchi, Chihiro Tsukano, Yoshiji Takemoto
ABSTRACT

The total synthesis of (-)-aurantioclavine (1) was accomplished based on an intramolecular asymmetric amination of allyl carbonate 3 containing a p-tosylamide group. The reaction using tris(dibenzylideneacetone)dipalladium(0), tBu-phosphinooxazoline, and Bu4NCl in CH2Cl2 gave azepane 2 in 77% yield with 95% enantiomeric excess. The obtained azepane 2 was also converted to a substructure of communesin F.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Tris(dibenzylideneacetone)dipalladium(0), 97%