Rhodium(I)-catalyzed carbonyl allenylation versus propargylation via redox transmetalation across tetragonal tin(II) oxide

Banerjee, Moloy ; Roy, Sujit (2004) Rhodium(I)-catalyzed carbonyl allenylation versus propargylation via redox transmetalation across tetragonal tin(II) oxide Organic Letters, 6 (13). pp. 2137-2140. ISSN 1523-7060

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Official URL: http://pubs.acs.org/doi/abs/10.1021/ol0493352

Related URL: http://dx.doi.org/10.1021/ol0493352

Abstract

A reagent combination of β-SnO and catalytic [Rh(COD)Cl]2 in THF-H2O promotes the reaction of propargyl bromides and aldehydes and directs the regioselectivity toward the formation of either allenic alcohols or homopropargylic alcohols. This highly regioselective either/or transformation proceeds via a transmetalation from rhodium to tin, in which metallotropic rearrangement between a propargylmetal and allenylmetal is arrested.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:42900
Deposited On:08 Jun 2011 06:18
Last Modified:08 Jun 2011 06:18

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