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

Aare Sreeshailam; Gandrath Dayaker; D. Venkata Ramana; Floris Chevallier; Thierry Roisnel; Shinsuke Komagawa; Ryo Takita; Masanobu Uchiyama; Palakodety Radha Krishna; Florence Mongin

doi:10.1039/C2RA21045B

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

Aare Sreeshailam,^ab Gandrath Dayaker,^ab D. Venkata Ramana,^ab Floris Chevallier,^a Thierry Roisnel,^c Shinsuke Komagawa,^de Ryo Takita,^de Masanobu Uchiyama,*^de Palakodety Radha Krishna*^b and Florence Mongin*^a

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* Corresponding authors

^a Chimie et Photonique Moléculaires, UMR 6226 Institut des Sciences Chimiques de Rennes, CNRS-Université de Rennes 1, Bâtiment 10A, Case 1003, Campus Scientifique de Beaulieu, Rennes, France
E-mail: florence.mongin@univ-rennes1.fr
Fax: +33-2-2323-6955.

^b D-211, Discovery Laboratory, Organic and Biomolecular Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad, India
E-mail: prkgenius@iict.res.in
Fax: +91-40-27160387.

^c Centre de Diffractométrie X, UMR 6226 Institut des Sciences Chimiques de Rennes, CNRS-Université de Rennes 1, Bâtiment 10B, Campus Scientifique de Beaulieu, Rennes, France

^d Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo, Japan
E-mail: uchiyama@mol.f.u-tokyo.ac.jp

^e Advanced Elements Chemistry Research Team, RIKEN-ASI, 2-1 Hirosawa, Wako-shi, Saitama, Japan

Abstract

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

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

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

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