Organic letters

Stereoselective Synthesis of Nipecotic Acid Derivatives via Palladium-Catalyzed Decarboxylative Cyclization of γ-Methylidene-δ-valerolactones with Imines

R Shintani, M Murakami, T Hayashi

Index: Shintani, Ryo; Murakami, Masataka; Hayashi, Tamio Organic Letters, 2009 , vol. 11, # 2 p. 457 - 459

Full Text: HTML

Citation Number: 31

Abstract

A new synthetic method of multisubstituted nipecotic acid (piperidine-3-carboxylic acid) derivatives has been developed by way of palladium-catalyzed decarboxylative cyclization of γ-methylidene-δ-valerolactones with imines. By employing the diethoxyphosphinoyl group as the N-protecting group for imines, the reaction proceeds smoothly with high diastereoselectivity. The products thus obtained can be further derivatized with high ...

Related Articles:

A facile one-pot benzylation of sodium enolates using trifluoromethanesulfonic anhydride and diphenyl sulfoxide

[Takuwa, Tomofumi; Minowa, Tomofumi; Fujisawa, Hidehiko; Mukaiyama, Teruaki Chemical and Pharmaceutical Bulletin, 2005 , vol. 53, # 5 p. 476 - 480]

Direct conversion of α, β-unsaturated nitriles into cyanohydrins using Mn (dpm) 3 catalyst, dioxygen and phenylsilane

[Magnus, Philip; Scott, David A.; Fielding, Mark R. Tetrahedron Letters, 2001 , vol. 42, # 25 p. 4127 - 4129]

Probing Persistent Intramolecular C− H··· X (X= O, S, Br, Cl, and F) Bonding in Solution Using Benzyl Meldrum's Acid Derivatives

[Fillion, Eric; Wilsily, Ashraf; Fishlock, Dan Journal of Organic Chemistry, 2009 , vol. 74, # 3 p. 1259 - 1267]

Sequential One-Pot Combination of Multireactions through Multicatalysis: A General Approach to Rapid Assembly of Functionalized Push− Pull Olefins, Phenols, and …

[Ramachary, Dhevalapally B.; Venkaiah, Chintalapudi; Reddy, Y. Vijayendar; Kishor, Mamillapalli Organic and Biomolecular Chemistry, 2009 , vol. 7, # 10 p. 2053 - 2062]

Photosilylation of electron-deficient alkenes by use of disilanes via photoinduced electron-transfer

[Mizuno, Kazuhiko; Nakanishi, Kazuhisa; Chosa, Jun-ichi; Nguyen, Tien; Otsuji, Yoshio Tetrahedron Letters, 1989 , vol. 30, # 28 p. 3689 - 3692]

More Articles...