Diastereoselective Access to Polyoxygenated Polycyclic Spirolactones through a Rhodium??Catalyzed [3+ 2] Cycloaddition Reaction: Experimental and Theoretical …

…, JL Parrain, G Chouraqui, L Commeiras

Index: Rodier, Fabien; Rajzmann, Michel; Parrain, Jean-Luc; Chouraqui, Gaelle; Commeiras, Laurent Chemistry - A European Journal, 2013 , vol. 19, # 7 p. 2467 - 2477

Full Text: HTML

Citation Number: 10

Abstract

Abstract The synthetic utility of γ-alkylidenebutenolides is demonstrated as highly competent dipolarophile partners in both intra-and intermolecular rhodium (II)-catalyzed 1, 3-dipolar cycloaddition reactions. The strength of this approach lies in the formation of spiro [6, 4] lactone moieties with the concomitant construction of quaternary spiro stereocenters. Typically, the construction of spirolactones involves an esterification step, which has often ...

Related Articles:

Intramolecular metallo-ene-allene reactions. A new carbocycles synthesis

[Meyer, Christophe; Marek, Ilane; Courtemanche, Gilles; Normant, Jean-F. Journal of Organic Chemistry, 1995 , vol. 60, # 4 p. 863 - 871]

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]

New One-Pot Synthesis of ò-Iodoalkyne

[Chakraborty, Arindam; Marek, Ilan Synthetic Communications, 2000 , vol. 30, # 11 p. 1895 - 1901]

Rh (I)-catalyzed intramolecular allenic Pauson-Khand reaction: Construction of a bicyclo [5.3. 0] dec-1, 7-dien-9-one skeleton

[Mukai, Chisato; Nomura, Izumi; Yamanishi, Kei; Hanaoka, Miyoji Organic Letters, 2002 , vol. 4, # 10 p. 1755 - 1758]

Efficient construction of the bicyclo [5.3. 0] decenone skeleton based on the Rh (I)-catalyzed allenic Pauson-Khand reaction

[Mukai, Chisato; Nomura, Izumi; Kitagaki, Shinji Journal of Organic Chemistry, 2003 , vol. 68, # 4 p. 1376 - 1385]

More Articles...