Addition of organometallic compounds to tin-containing cyclic ketones. Remote stereocontrol induced by the stannyl group
A Barbero, FJ Pulido, JA Rincón
Index: Barbero, Asuncion; Pulido, Francisco J.; Rincon, Juan A. Journal of the American Chemical Society, 2003 , vol. 125, # 39 p. 12049 - 12056
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Citation Number: 12
Abstract
The addition of organometallic reagents to cyclic ketones bearing stannyl groups at an appropriate distance to the carbonyl group occurs with a high level of stereocontrol, giving alcohols resulting from attack of the nucleophile syn to the tin center. This remarkable remote control is a consequence of the anchoring of the organometallic reagent by the tin and carbonyl groups. The degree of selectivity observed depends on the spatial distance ...
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