An optically pure (+)-S-Halostachine analogue 5a was synthesized in 57% total yield and in three steps from optically pure(-)-aR-[o-tolualdehyde]-chromium-tricarbonyl complex 2a. Various optically pure Halostachine analogues having an ortho-substituted aromatic ring and of both configurations (R and S) are thus available by this route. An X-ray structure of the intermediate complexed oxazoline 3bI allowed to confirm the model we proposed for the approach of a nucleophile on these arene complexes.

A 3-STEP SYNTHESIS OF AN ENANTIOMERICALLY PURE HALOSTACHINE ANALOG STARTING FROM ETA-6-(ORTHO-TOLUALDEHYDE)-CHROMIUM-TRICARBONYL / A. SOLLADIE-CAVALLO, S. QUAZZOTTI, S. COLONNA, A. MANFREDI, J. FISCHER, A. DECIAN. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - 3:2(1992), pp. 287-296. [10.1016/S0957-4166(00)80208-6]

A 3-STEP SYNTHESIS OF AN ENANTIOMERICALLY PURE HALOSTACHINE ANALOG STARTING FROM ETA-6-(ORTHO-TOLUALDEHYDE)-CHROMIUM-TRICARBONYL

S. COLONNA;A. MANFREDI;
1992

Abstract

An optically pure (+)-S-Halostachine analogue 5a was synthesized in 57% total yield and in three steps from optically pure(-)-aR-[o-tolualdehyde]-chromium-tricarbonyl complex 2a. Various optically pure Halostachine analogues having an ortho-substituted aromatic ring and of both configurations (R and S) are thus available by this route. An X-ray structure of the intermediate complexed oxazoline 3bI allowed to confirm the model we proposed for the approach of a nucleophile on these arene complexes.
CHROMIUM-TRICARBONYL; COMPLEXES; RESOLUTION
Settore CHIM/06 - Chimica Organica
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/187650
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