Synthesis of both enantiomers of ferrocene[1,2-c]1H-quinolin-2-one by diastereoselective deproto-zincation of sugar-derived ferrocene esters

Aare Sreeshailam (1) , Gandrath Dayaker (1) , D. Venkata Ramana (1) , Floris Chevallier (1) , Thierry Roisnel (1) , Shinsuke Komagawa (2) , Ryo Takita (2) , Masanobu Uchiyama (2) , Palakodety Radha Krishna (3) , Florence Mongin (1)

1 ISCR - Institut des Sciences Chimiques de Rennes
2 RIKEN - RIKEN - Institute of Physical and Chemical Research [Japon]
3 Organic Chemistry Division-III

Diastereoselective deproto-metallation of several sugar-derived ferrocene esters using lithium-zinc bases was studied. While bis[(R)-1-phenylethyl]amino as ligand afforded the diacetone-D-glucose-based (SP)-2-iodoferrocene ester in 91% de after iodination, the RP was synthesized from α-D-glucofuranose using 2,2,6,6-tetramethylpiperidino as ligand. Both (RP)- and (SP)-ferrocene[1,2-c]1H-quinolin-2-one were reached by subsequent cyclizing coupling, albeit their racemization was noted.

Domains: Chemical Sciences; Organic chemistry; Chemical Sciences; Theoretical and/or physical chemistry

Aare Sreeshailam, Gandrath Dayaker, D. Venkata Ramana, Floris Chevallier, Thierry Roisnel, et al.. Synthesis of both enantiomers of ferrocene[1,2-c]1H-quinolin-2-one by diastereoselective deproto-zincation of sugar-derived ferrocene esters. RSC Advances, 2012, 2, pp.7030-7032. ⟨10.1039/c2ra21045b⟩. ⟨hal-01053780⟩