The intramolecular cycloaddition to vinyl sulphur derivatives of a series of nitrones featuring an alkyl or alkoxy substituted α-stereocenter on the tether connecting dipole and dipolarophile occurs in a completely stereoselective fashion to give 3′,3-anti configurated products. The synthetic potentialities of this reaction is illustrated by the synthesis of a precursor of (d)-biotin.
STEREOCONTROL IN THE INTRAMOLECULAR NITRONE CYCLOADDITION TO VINYL SULFUR DERIVATIVES / R. ANNUNZIATA, M. CINQUINI, F. COZZI, P. GIARONI, L. RAIMONDI. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - 1:4(1990), pp. 251-264. [10.1016/S0957-4166(00)86330-2]
STEREOCONTROL IN THE INTRAMOLECULAR NITRONE CYCLOADDITION TO VINYL SULFUR DERIVATIVES
R. ANNUNZIATAPrimo
;M. CINQUINISecondo
;F. COZZI;L. RAIMONDIUltimo
1990
Abstract
The intramolecular cycloaddition to vinyl sulphur derivatives of a series of nitrones featuring an alkyl or alkoxy substituted α-stereocenter on the tether connecting dipole and dipolarophile occurs in a completely stereoselective fashion to give 3′,3-anti configurated products. The synthetic potentialities of this reaction is illustrated by the synthesis of a precursor of (d)-biotin.
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