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Desymmetrization of meso-dienyne by asymmetric Pauson-Khand type reaction catalysts.

Chemical communications (Cambridge, England) (2004-04-30)
Nakcheol Jeong, Dong Hoon Kim, Jun Hun Choi
ABSTRACT

Desymmetrization of the meso dienynes, such as propargyl 1-vinylallyl N-tosylamides (1a-c) and propargyl 1-vinylallyl ethers (1d-e), by asymmetric Pauson-Khand type reaction catalysts was studied. The corresponding vinyl substituted bicyclic pentenones (2 and 3) were obtained with high diastereoselectivity and enantioselectivity.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
1,4-Pentadien-3-ol, contains 0.4% hydroquinone as stabilizer, ≥96%
Sigma-Aldrich
(R)-(+)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene, 97%