Remote Stereocontrol in Carbonyl Additions Promoted by Vinylstannanes

Asunción Barbero; Francisco J Pulido; Juan A Rincón; Purificación Cuadrado; Diego Galisteo; Henar Martínez-García

doi:10.1002/1521-3773(20010601)40:11<2101::AID-ANIE2101>3.0.CO;2-H

Remote Stereocontrol in Carbonyl Additions Promoted by Vinylstannanes

Angew Chem Int Ed Engl. 2001 Jun 1;40(11):2101-2103. doi: 10.1002/1521-3773(20010601)40:11<2101::AID-ANIE2101>3.0.CO;2-H.

Authors

Asunción Barbero¹, Francisco J Pulido¹, Juan A Rincón¹, Purificación Cuadrado¹, Diego Galisteo¹, Henar Martínez-García¹

Affiliation

¹ Departamento de Química Orgánica, Universidad de Valladolid 47011 Valladolid (Spain) Fax: (+34) 983-423013.

PMID: 29712185
DOI: 10.1002/1521-3773(20010601)40:11<2101::AID-ANIE2101>3.0.CO;2-H

Abstract

syn to tin is the preferred mode of addition of organolithium reagents to the carbonyl group of cyclic ketones with a β-stannylvinyl group. This remarkable remote control is a consequence of the anchoring of the organolithium reagent by the tin and carbonyl groups.

Keywords: alkenes; cuprates; diastereoselectivity; ketones; tin.