Organic letters

Atom-Economical Synthesis of Functionalized Cycloalkanes via Catalytic Redox Cycloisomerization of Propargyl Alcohols

BM Trost, A Breder, B Kai

Index: Trost, Barry M.; Breder, Alexander; Kai, Bao Organic Letters, 2012 , vol. 14, # 7 p. 1708 - 1711

Full Text: HTML

Citation Number: 9

Abstract

An atom-economical procedure for the direct synthesis of cycloalkanes from propargyl alcohols is reported. This high-yielding one-pot process involves a sequence consisting of a Ru-catalyzed redox isomerization of ynols into enones or an enal followed by an intramolecular Michael addition of a variety of carbon nucleophiles. Furthermore, an asymmetric variant of this protocol realized by the aid of a chiral nonracemic diamine ...

Related Articles:

Design, synthesis, and BK channel-opening activity of hexahydrodibenzazepinone derivatives

[Tashima, Toshihiko; Toriumi, Yoshimi; Mochizuki, Yumi; Nonomura, Taro; Nagaoka, Satoru; Furukawa, Katsuo; Tsuru, Hiromichi; Adachi-Akahane, Satomi; Ohwada, Tomohiko Bioorganic and Medicinal Chemistry, 2006 , vol. 14, # 23 p. 8014 - 8031]

Ag-mediated reactions: Coupling and heterocyclization reactions

[Boaventura, Maria-Amelia; Drouin, Jacques Bulletin de la Societe Chimique de France, 1987 , # 6 p. 1015 - 1026]

Strong base-induced intramolecular cycloaddition of homophthalic anhydrides: an efficient synthesis of polycyclic peri-hydroxy aromatic compounds

[Kita, Yasuyuki; Okunaka, Ryuichi; Honda, Takao; Shindo, Miki; Taniguchi, Miyako; et al. Journal of Organic Chemistry, 1991 , vol. 56, # 1 p. 119 - 125]

More Articles...