Chiral copper complexes of BINOL- and TADDOL derived phosphorus amidites proved to be highly effective catalysts for the alkylation of alkynyl epoxides with dialkylzinc reagents. The corresponding alpha-allenol reaction products (S(N)2'-pathway) were obtained with good to excellent regio- and diastereoselectivity. The e.e. values obtained for this reaction were in the range of 26-38 %. A number of different Cu(II)-complexes were screened as possible catalysts and the results obtained indicate a complete control of the diastereoselectivity with an easy access to both enantioenriched syn and anti-alpha-allenols. (C) 1999 Elsevier Science Ltd. All rights reserved.

A new diastereo- and enantioselective copper-catalyzed conversion of alkynyl epoxides into alpha-allenic alcohols.

CROTTI, PAOLO;PINESCHI, MAURO;
1999

Abstract

Chiral copper complexes of BINOL- and TADDOL derived phosphorus amidites proved to be highly effective catalysts for the alkylation of alkynyl epoxides with dialkylzinc reagents. The corresponding alpha-allenol reaction products (S(N)2'-pathway) were obtained with good to excellent regio- and diastereoselectivity. The e.e. values obtained for this reaction were in the range of 26-38 %. A number of different Cu(II)-complexes were screened as possible catalysts and the results obtained indicate a complete control of the diastereoselectivity with an easy access to both enantioenriched syn and anti-alpha-allenols. (C) 1999 Elsevier Science Ltd. All rights reserved.
Bertozzi, F; Crotti, Paolo; Macchia, F; Pineschi, Mauro; Arnold, A; Feringa, Bl
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11568/203404
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